# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H40 Fe2 N16 Ni O2, 2(H2 O)' _chemical_formula_sum 'C48 H44 Fe2 N16 Ni O4' _chemical_formula_weight 1079.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3769(16) _cell_length_b 10.441(2) _cell_length_c 14.992(3) _cell_angle_alpha 90.311(2) _cell_angle_beta 106.740(3) _cell_angle_gamma 104.011(2) _cell_volume 1359.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3725 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 23.85 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7799 _exptl_absorpt_correction_T_max 0.8208 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12576 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0799 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.91 _reflns_number_total 5140 _reflns_number_gt 3169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.05P)^2^+0.66P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5140 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4907(5) 0.6895(4) 0.3277(3) 0.0464(10) Uani 1 1 d . . . C2 C 0.2669(5) 0.6061(4) 0.1764(3) 0.0509(10) Uani 1 1 d . . . C3 C 0.5932(5) 0.9322(5) 0.2656(3) 0.0505(10) Uani 1 1 d . . . C4 C 0.6649(5) 0.6186(4) 0.1970(3) 0.0491(10) Uani 1 1 d . . . H4 H 0.6718 0.5974 0.2594 0.059 Uiso 1 1 calc R . . C5 C 0.7541(5) 0.5697(4) 0.1511(3) 0.0565(11) Uani 1 1 d . . . H5 H 0.8176 0.5150 0.1818 0.068 Uiso 1 1 calc R . . C6 C 0.7492(5) 0.6011(4) 0.0621(3) 0.0557(11) Uani 1 1 d . . . H6 H 0.8117 0.5710 0.0311 0.067 Uiso 1 1 calc R . . C7 C 0.6490(5) 0.6797(4) 0.0164(3) 0.0491(10) Uani 1 1 d . . . C8 C 0.6359(5) 0.7229(4) -0.0749(3) 0.0520(10) Uani 1 1 d . . . H8 H 0.6971 0.6991 -0.1097 0.062 Uiso 1 1 calc R . . C9 C 0.5386(5) 0.7966(4) -0.1122(3) 0.0560(11) Uani 1 1 d . . . H9 H 0.5323 0.8246 -0.1730 0.067 Uiso 1 1 calc R . . C10 C 0.4455(5) 0.8334(4) -0.0635(3) 0.0545(11) Uani 1 1 d . . . H10 H 0.3754 0.8837 -0.0928 0.065 Uiso 1 1 calc R . . C11 C 0.4539(5) 0.7980(4) 0.0263(3) 0.0501(10) Uani 1 1 d . . . C12 C 0.5617(5) 0.7215(4) 0.0674(3) 0.0490(10) Uani 1 1 d . . . C13 C 0.2469(5) 0.8694(4) 0.0589(3) 0.0457(9) Uani 1 1 d . . . C14 C 0.1848(5) 0.8837(4) 0.1390(3) 0.0480(10) Uani 1 1 d . . . C15 C 0.0481(5) 0.9224(4) 0.1262(3) 0.0509(10) Uani 1 1 d . . . H15 H -0.0074 0.9393 0.0655 0.061 Uiso 1 1 calc R . . C16 C -0.0066(5) 0.9363(4) 0.1994(3) 0.0515(10) Uani 1 1 d . . . H16 H -0.1043 0.9541 0.1901 0.062 Uiso 1 1 calc R . . C17 C 0.0886(5) 0.9231(4) 0.2917(3) 0.0458(9) Uani 1 1 d . . . C18 C 0.0486(5) 0.9429(4) 0.3707(3) 0.0542(11) Uani 1 1 d . . . H18 H -0.0493 0.9587 0.3644 0.065 Uiso 1 1 calc R . . C19 C 0.1447(5) 0.9407(4) 0.4579(3) 0.0528(11) Uani 1 1 d . . . H19 H 0.1160 0.9591 0.5114 0.063 Uiso 1 1 calc R . . C20 C 0.2847(5) 0.9115(4) 0.4679(3) 0.0484(10) Uani 1 1 d . . . H20 H 0.3521 0.9116 0.5289 0.058 Uiso 1 1 calc R . . C21 C 0.3279(5) 0.8827(4) 0.3926(3) 0.0530(11) Uani 1 1 d . . . H21 H 0.4233 0.8607 0.4010 0.064 Uiso 1 1 calc R . . C22 C 0.2273(5) 0.8859(4) 0.2994(3) 0.0490(10) Uani 1 1 d . . . C23 C 0.4969(5) 0.6938(5) 0.6388(3) 0.0574(11) Uani 1 1 d . . . H23A H 0.4940 0.6437 0.6944 0.069 Uiso 1 1 calc R . . H23B H 0.4653 0.7759 0.6469 0.069 Uiso 1 1 calc R . . C24 C 0.6568(5) 0.7289(4) 0.6320(3) 0.0512(10) Uani 1 1 d . . . H24A H 0.6662 0.7996 0.5888 0.061 Uiso 1 1 calc R . . H24B H 0.7291 0.7647 0.6943 0.061 Uiso 1 1 calc R . . Fe1 Fe 0.43181(7) 0.76981(6) 0.20903(4) 0.04530(19) Uani 1 1 d . . . N1 N 0.5207(4) 0.6345(3) 0.3948(2) 0.0438(8) Uani 1 1 d . . . N2 N 0.1721(4) 0.5105(4) 0.1596(3) 0.0590(10) Uani 1 1 d . . . N3 N 0.6844(4) 1.0298(4) 0.2979(3) 0.0551(9) Uani 1 1 d . . . N4 N 0.5722(4) 0.6922(3) 0.1578(2) 0.0510(9) Uani 1 1 d . . . N5 N 0.3744(4) 0.8250(3) 0.0844(2) 0.0468(8) Uani 1 1 d . . . N6 N 0.2715(4) 0.8596(3) 0.2228(2) 0.0440(8) Uani 1 1 d . . . N7 N 0.3919(4) 0.6164(3) 0.5578(2) 0.0515(9) Uani 1 1 d . . . H7A H 0.3538 0.6712 0.5145 0.062 Uiso 1 1 calc R . . H7B H 0.3105 0.5627 0.5733 0.062 Uiso 1 1 calc R . . N8 N 0.7017(4) 0.6168(4) 0.5992(3) 0.0568(9) Uani 1 1 d . . . H8A H 0.7366 0.5684 0.6481 0.068 Uiso 1 1 calc R . . H8B H 0.7786 0.6460 0.5718 0.068 Uiso 1 1 calc R . . Ni1 Ni 0.5000 0.5000 0.5000 0.0466(2) Uani 1 2 d S . . O1 O 0.1799(3) 0.8966(3) -0.01945(19) 0.0519(7) Uani 1 1 d . . . O1W O 0.0083(8) 0.2659(7) 0.1802(5) 0.057(2) Uani 0.40 1 d P . . H1X H -0.0469 0.2120 0.1334 0.069 Uiso 0.40 1 d PR . . H1Y H 0.0821 0.3177 0.1659 0.069 Uiso 0.40 1 d PR . . O2W O 0.0770(10) 0.7317(8) 0.6612(6) 0.051(2) Uani 0.30 1 d P . . H2X H -0.0060 0.7464 0.6865 0.061 Uiso 0.30 1 d PR . . H2Y H 0.1208 0.8112 0.6835 0.061 Uiso 0.30 1 d PR . . O3W O 0.1252(10) 0.5026(10) 0.6199(6) 0.052(2) Uani 0.30 1 d P . . H3X H 0.0703 0.4405 0.6411 0.062 Uiso 0.30 1 d PR . . H3Y H 0.1090 0.5762 0.6329 0.062 Uiso 0.30 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(2) 0.058(3) 0.036(2) 0.0072(19) 0.0087(17) 0.014(2) C2 0.058(3) 0.042(2) 0.054(3) 0.011(2) 0.015(2) 0.017(2) C3 0.047(2) 0.061(3) 0.044(2) 0.014(2) 0.0151(19) 0.013(2) C4 0.048(2) 0.044(2) 0.060(3) 0.0147(19) 0.016(2) 0.020(2) C5 0.058(3) 0.053(3) 0.059(3) 0.011(2) 0.013(2) 0.019(2) C6 0.049(2) 0.056(3) 0.060(3) 0.010(2) 0.015(2) 0.011(2) C7 0.051(2) 0.055(3) 0.048(2) 0.009(2) 0.020(2) 0.020(2) C8 0.056(3) 0.057(3) 0.053(3) 0.013(2) 0.022(2) 0.023(2) C9 0.054(3) 0.062(3) 0.046(2) 0.012(2) 0.011(2) 0.008(2) C10 0.050(2) 0.062(3) 0.053(3) 0.009(2) 0.014(2) 0.017(2) C11 0.050(2) 0.055(3) 0.044(2) 0.0077(19) 0.0121(19) 0.013(2) C12 0.053(2) 0.050(2) 0.045(2) 0.0021(19) 0.0136(19) 0.016(2) C13 0.051(2) 0.050(2) 0.033(2) 0.0079(18) 0.0092(18) 0.012(2) C14 0.055(3) 0.049(2) 0.039(2) 0.0105(18) 0.0086(18) 0.018(2) C15 0.042(2) 0.068(3) 0.047(2) 0.017(2) 0.0162(18) 0.016(2) C16 0.056(3) 0.058(3) 0.053(3) 0.007(2) 0.022(2) 0.031(2) C17 0.046(2) 0.046(2) 0.045(2) 0.0133(18) 0.0120(18) 0.0141(19) C18 0.060(3) 0.060(3) 0.054(3) 0.011(2) 0.023(2) 0.029(2) C19 0.056(3) 0.056(3) 0.046(2) 0.009(2) 0.015(2) 0.014(2) C20 0.061(3) 0.047(2) 0.042(2) 0.0103(18) 0.0170(19) 0.019(2) C21 0.058(3) 0.058(3) 0.054(3) 0.009(2) 0.020(2) 0.031(2) C22 0.063(3) 0.050(2) 0.036(2) 0.0080(18) 0.0132(19) 0.019(2) C23 0.060(3) 0.062(3) 0.058(3) 0.013(2) 0.020(2) 0.025(2) C24 0.045(2) 0.047(2) 0.063(3) 0.015(2) 0.013(2) 0.018(2) Fe1 0.0547(4) 0.0489(4) 0.0371(3) 0.0144(3) 0.0134(3) 0.0220(3) N1 0.0479(19) 0.056(2) 0.0411(18) 0.0126(15) 0.0187(15) 0.0323(17) N2 0.060(2) 0.060(3) 0.052(2) -0.0047(19) 0.0177(18) 0.006(2) N3 0.048(2) 0.055(2) 0.058(2) 0.0049(19) 0.0124(18) 0.0099(19) N4 0.058(2) 0.058(2) 0.048(2) 0.0151(17) 0.0222(17) 0.0288(19) N5 0.056(2) 0.052(2) 0.0384(18) 0.0099(15) 0.0171(16) 0.0217(18) N6 0.056(2) 0.0354(17) 0.0450(19) 0.0092(14) 0.0180(16) 0.0149(16) N7 0.049(2) 0.055(2) 0.051(2) 0.0099(17) 0.0133(17) 0.0160(18) N8 0.058(2) 0.059(2) 0.054(2) 0.0059(18) 0.0089(18) 0.0245(19) Ni1 0.0562(5) 0.0556(5) 0.0339(4) 0.0113(3) 0.0139(3) 0.0243(4) O1 0.0525(17) 0.0539(17) 0.0453(16) 0.0159(13) 0.0053(13) 0.0172(14) O1W 0.056(4) 0.046(4) 0.054(4) 0.012(3) 0.017(3) -0.017(4) O2W 0.052(6) 0.035(5) 0.050(5) -0.004(4) 0.021(4) -0.023(4) O3W 0.045(5) 0.055(6) 0.058(6) 0.017(5) 0.017(4) 0.016(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.158(5) . ? C1 Fe1 1.962(4) . ? C2 N2 1.135(5) . ? C2 Fe1 1.957(5) . ? C3 N3 1.157(5) . ? C3 Fe1 1.971(5) . ? C4 N4 1.313(5) . ? C4 C5 1.403(6) . ? C4 H4 0.9500 . ? C5 C6 1.366(6) . ? C5 H5 0.9500 . ? C6 C7 1.427(6) . ? C6 H6 0.9500 . ? C7 C12 1.406(6) . ? C7 C8 1.424(6) . ? C8 C9 1.337(6) . ? C8 H8 0.9500 . ? C9 C10 1.403(6) . ? C9 H9 0.9500 . ? C10 C11 1.383(6) . ? C10 H10 0.9500 . ? C11 N5 1.367(5) . ? C11 C12 1.441(6) . ? C12 N4 1.372(5) . ? C13 O1 1.233(4) . ? C13 N5 1.341(5) . ? C13 C14 1.498(6) . ? C14 N6 1.348(5) . ? C14 C15 1.398(5) . ? C15 C16 1.359(6) . ? C15 H15 0.9500 . ? C16 C17 1.443(6) . ? C16 H16 0.9500 . ? C17 C18 1.370(6) . ? C17 C22 1.419(6) . ? C18 C19 1.361(6) . ? C18 H18 0.9500 . ? C19 C20 1.385(6) . ? C19 H19 0.9500 . ? C20 C21 1.360(6) . ? C20 H20 0.9500 . ? C21 C22 1.449(6) . ? C21 H21 0.9500 . ? C22 N6 1.374(5) . ? C23 N7 1.419(5) . ? C23 C24 1.488(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N8 1.463(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? Fe1 N5 1.922(3) . ? Fe1 N6 2.010(3) . ? Fe1 N4 2.018(3) . ? N1 Ni1 2.137(3) . ? N7 Ni1 2.085(3) . ? N7 H7A 0.9200 . ? N7 H7B 0.9200 . ? N8 Ni1 2.126(4) . ? N8 H8A 0.9200 . ? N8 H8B 0.9200 . ? Ni1 N7 2.085(3) 2_666 ? Ni1 N8 2.126(4) 2_666 ? Ni1 N1 2.137(3) 2_666 ? O1W H1X 0.8500 . ? O1W H1Y 0.8500 . ? O2W H2X 1.0000 . ? O2W H2Y 0.8500 . ? O3W H3X 0.8501 . ? O3W H3Y 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 Fe1 175.8(4) . . ? N2 C2 Fe1 178.4(4) . . ? N3 C3 Fe1 177.8(4) . . ? N4 C4 C5 123.1(4) . . ? N4 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C6 C5 C4 119.7(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 119.1(4) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C12 C7 C8 118.1(4) . . ? C12 C7 C6 116.9(4) . . ? C8 C7 C6 125.0(4) . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 121.6(4) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 121.2(4) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N5 C11 C10 129.7(4) . . ? N5 C11 C12 113.1(3) . . ? C10 C11 C12 117.2(4) . . ? N4 C12 C7 122.9(4) . . ? N4 C12 C11 116.1(4) . . ? C7 C12 C11 121.0(4) . . ? O1 C13 N5 127.9(4) . . ? O1 C13 C14 119.9(4) . . ? N5 C13 C14 112.3(3) . . ? N6 C14 C15 123.4(4) . . ? N6 C14 C13 115.3(3) . . ? C15 C14 C13 121.3(3) . . ? C16 C15 C14 120.9(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 117.8(4) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C18 C17 C22 119.7(4) . . ? C18 C17 C16 122.5(4) . . ? C22 C17 C16 117.9(4) . . ? C19 C18 C17 122.0(4) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C18 C19 C20 119.5(4) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 121.6(4) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? N6 C22 C17 122.7(4) . . ? N6 C22 C21 119.8(4) . . ? C17 C22 C21 117.5(4) . . ? N7 C23 C24 111.4(4) . . ? N7 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N7 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? N8 C24 C23 113.4(4) . . ? N8 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? N8 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? N5 Fe1 C2 92.59(16) . . ? N5 Fe1 C1 171.78(16) . . ? C2 Fe1 C1 82.38(17) . . ? N5 Fe1 C3 96.87(16) . . ? C2 Fe1 C3 169.18(17) . . ? C1 Fe1 C3 88.79(17) . . ? N5 Fe1 N6 82.17(13) . . ? C2 Fe1 N6 86.58(15) . . ? C1 Fe1 N6 103.91(15) . . ? C3 Fe1 N6 89.50(16) . . ? N5 Fe1 N4 81.81(13) . . ? C2 Fe1 N4 92.89(16) . . ? C1 Fe1 N4 91.92(15) . . ? C3 Fe1 N4 93.65(17) . . ? N6 Fe1 N4 163.93(13) . . ? C1 N1 Ni1 161.5(3) . . ? C4 N4 C12 118.2(4) . . ? C4 N4 Fe1 129.9(3) . . ? C12 N4 Fe1 111.9(3) . . ? C13 N5 C11 125.7(3) . . ? C13 N5 Fe1 116.7(3) . . ? C11 N5 Fe1 116.9(3) . . ? C14 N6 C22 116.9(3) . . ? C14 N6 Fe1 111.3(3) . . ? C22 N6 Fe1 131.4(3) . . ? C23 N7 Ni1 110.7(3) . . ? C23 N7 H7A 109.5 . . ? Ni1 N7 H7A 109.5 . . ? C23 N7 H7B 109.5 . . ? Ni1 N7 H7B 109.5 . . ? H7A N7 H7B 108.1 . . ? C24 N8 Ni1 105.9(2) . . ? C24 N8 H8A 110.6 . . ? Ni1 N8 H8A 110.6 . . ? C24 N8 H8B 110.6 . . ? Ni1 N8 H8B 110.6 . . ? H8A N8 H8B 108.7 . . ? N7 Ni1 N7 180.0 2_666 . ? N7 Ni1 N8 82.95(14) 2_666 2_666 ? N7 Ni1 N8 97.05(14) . 2_666 ? N7 Ni1 N8 97.05(14) 2_666 . ? N7 Ni1 N8 82.95(14) . . ? N8 Ni1 N8 180.0 2_666 . ? N7 Ni1 N1 89.03(12) 2_666 . ? N7 Ni1 N1 90.97(12) . . ? N8 Ni1 N1 87.59(14) 2_666 . ? N8 Ni1 N1 92.41(14) . . ? N7 Ni1 N1 90.97(12) 2_666 2_666 ? N7 Ni1 N1 89.03(12) . 2_666 ? N8 Ni1 N1 92.41(14) 2_666 2_666 ? N8 Ni1 N1 87.59(14) . 2_666 ? N1 Ni1 N1 180.0 . 2_666 ? H1X O1W H1Y 109.5 . . ? H2X O2W H2Y 83.0 . . ? H3X O3W H3Y 109.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C4 C5 C6 1.5(7) . . . . ? C4 C5 C6 C7 -2.1(6) . . . . ? C5 C6 C7 C12 0.7(6) . . . . ? C5 C6 C7 C8 178.0(4) . . . . ? C12 C7 C8 C9 -2.7(6) . . . . ? C6 C7 C8 C9 -180.0(4) . . . . ? C7 C8 C9 C10 -0.3(7) . . . . ? C8 C9 C10 C11 1.8(7) . . . . ? C9 C10 C11 N5 179.6(4) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C8 C7 C12 N4 -176.1(4) . . . . ? C6 C7 C12 N4 1.4(6) . . . . ? C8 C7 C12 C11 4.3(6) . . . . ? C6 C7 C12 C11 -178.2(4) . . . . ? N5 C11 C12 N4 -2.3(5) . . . . ? C10 C11 C12 N4 177.5(4) . . . . ? N5 C11 C12 C7 177.3(4) . . . . ? C10 C11 C12 C7 -2.9(6) . . . . ? O1 C13 C14 N6 -176.0(4) . . . . ? N5 C13 C14 N6 4.6(5) . . . . ? O1 C13 C14 C15 2.6(6) . . . . ? N5 C13 C14 C15 -176.8(4) . . . . ? N6 C14 C15 C16 -0.9(7) . . . . ? C13 C14 C15 C16 -179.4(4) . . . . ? C14 C15 C16 C17 6.2(6) . . . . ? C15 C16 C17 C18 176.1(4) . . . . ? C15 C16 C17 C22 -5.0(6) . . . . ? C22 C17 C18 C19 6.5(7) . . . . ? C16 C17 C18 C19 -174.6(4) . . . . ? C17 C18 C19 C20 -3.1(7) . . . . ? C18 C19 C20 C21 -1.1(7) . . . . ? C19 C20 C21 C22 1.6(6) . . . . ? C18 C17 C22 N6 177.5(4) . . . . ? C16 C17 C22 N6 -1.4(6) . . . . ? C18 C17 C22 C21 -5.7(6) . . . . ? C16 C17 C22 C21 175.4(4) . . . . ? C20 C21 C22 N6 178.6(4) . . . . ? C20 C21 C22 C17 1.7(6) . . . . ? N7 C23 C24 N8 -46.0(5) . . . . ? C5 C4 N4 C12 0.5(6) . . . . ? C5 C4 N4 Fe1 178.8(3) . . . . ? C7 C12 N4 C4 -2.1(6) . . . . ? C11 C12 N4 C4 177.6(4) . . . . ? C7 C12 N4 Fe1 179.4(3) . . . . ? C11 C12 N4 Fe1 -0.9(5) . . . . ? N5 Fe1 N4 C4 -175.6(4) . . . . ? C2 Fe1 N4 C4 -83.4(4) . . . . ? C1 Fe1 N4 C4 -1.0(4) . . . . ? C3 Fe1 N4 C4 87.9(4) . . . . ? N6 Fe1 N4 C4 -171.1(4) . . . . ? N5 Fe1 N4 C12 2.7(3) . . . . ? C2 Fe1 N4 C12 94.9(3) . . . . ? C1 Fe1 N4 C12 177.4(3) . . . . ? C3 Fe1 N4 C12 -93.7(3) . . . . ? N6 Fe1 N4 C12 7.2(7) . . . . ? O1 C13 N5 C11 -1.7(7) . . . . ? C14 C13 N5 C11 177.7(4) . . . . ? O1 C13 N5 Fe1 -171.8(4) . . . . ? C14 C13 N5 Fe1 7.6(4) . . . . ? C10 C11 N5 C13 14.9(7) . . . . ? C12 C11 N5 C13 -165.4(4) . . . . ? C10 C11 N5 Fe1 -175.0(4) . . . . ? C12 C11 N5 Fe1 4.7(5) . . . . ? C2 Fe1 N5 C13 74.3(3) . . . . ? C3 Fe1 N5 C13 -100.4(3) . . . . ? N6 Fe1 N5 C13 -11.9(3) . . . . ? N4 Fe1 N5 C13 166.8(3) . . . . ? C2 Fe1 N5 C11 -96.7(3) . . . . ? C3 Fe1 N5 C11 88.5(3) . . . . ? N6 Fe1 N5 C11 177.1(3) . . . . ? N4 Fe1 N5 C11 -4.2(3) . . . . ? C15 C14 N6 C22 -5.5(6) . . . . ? C13 C14 N6 C22 173.0(3) . . . . ? C15 C14 N6 Fe1 167.8(3) . . . . ? C13 C14 N6 Fe1 -13.6(4) . . . . ? C17 C22 N6 C14 6.6(6) . . . . ? C21 C22 N6 C14 -170.1(4) . . . . ? C17 C22 N6 Fe1 -165.2(3) . . . . ? C21 C22 N6 Fe1 18.1(6) . . . . ? N5 Fe1 N6 C14 13.8(3) . . . . ? C2 Fe1 N6 C14 -79.3(3) . . . . ? C1 Fe1 N6 C14 -160.6(3) . . . . ? C3 Fe1 N6 C14 110.8(3) . . . . ? N4 Fe1 N6 C14 9.3(7) . . . . ? N5 Fe1 N6 C22 -174.1(4) . . . . ? C2 Fe1 N6 C22 92.8(4) . . . . ? C1 Fe1 N6 C22 11.6(4) . . . . ? C3 Fe1 N6 C22 -77.1(4) . . . . ? N4 Fe1 N6 C22 -178.6(5) . . . . ? C24 C23 N7 Ni1 30.9(4) . . . . ? C23 C24 N8 Ni1 35.4(4) . . . . ? C23 N7 Ni1 N8 170.8(3) . . . 2_666 ? C23 N7 Ni1 N8 -9.2(3) . . . . ? C23 N7 Ni1 N1 -101.5(3) . . . . ? C23 N7 Ni1 N1 78.5(3) . . . 2_666 ? C24 N8 Ni1 N7 165.9(3) . . . 2_666 ? C24 N8 Ni1 N7 -14.1(3) . . . . ? C24 N8 Ni1 N1 76.6(3) . . . . ? C24 N8 Ni1 N1 -103.4(3) . . . 2_666 ? C1 N1 Ni1 N7 101.6(10) . . . 2_666 ? C1 N1 Ni1 N7 -78.4(10) . . . . ? C1 N1 Ni1 N8 18.6(10) . . . 2_666 ? C1 N1 Ni1 N8 -161.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.91 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.508 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 948658' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H60 Fe2 N16 Ni O2, 2(C3 H7 N O), 2(H2 O)' _chemical_formula_sum 'C66 H78 Fe2 N18 Ni O6' _chemical_formula_weight 1389.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.8501(15) _cell_length_b 16.246(2) _cell_length_c 19.5463(13) _cell_angle_alpha 90.00 _cell_angle_beta 121.075(4) _cell_angle_gamma 90.00 _cell_volume 7030.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3912 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 23.57 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2912 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7 _exptl_absorpt_correction_T_max 0.8 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16527 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 26.03 _reflns_number_total 6759 _reflns_number_gt 5101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.07P)^2^+1.99P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6759 _refine_ls_number_parameters 435 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.43052(13) 0.05506(18) -0.01445(18) 0.0426(7) Uani 1 1 d . . . H1 H 0.4039 0.0761 -0.0650 0.051 Uiso 1 1 calc R . . C2 C 0.43560(14) -0.0322(2) 0.00008(19) 0.0484(8) Uani 1 1 d . . . H2 H 0.4122 -0.0671 -0.0427 0.058 Uiso 1 1 calc R . . C3 C 0.47289(14) -0.0663(2) 0.07313(19) 0.0485(8) Uani 1 1 d . . . H3 H 0.4747 -0.1230 0.0804 0.058 Uiso 1 1 calc R . . C4 C 0.50967(15) -0.01122(19) 0.1391(2) 0.0498(8) Uani 1 1 d . . . C5 C 0.54864(14) -0.0375(2) 0.21557(19) 0.0477(7) Uani 1 1 d . . . H5 H 0.5551 -0.0934 0.2273 0.057 Uiso 1 1 calc R . . C6 C 0.57932(13) 0.02306(19) 0.27706(18) 0.0441(7) Uani 1 1 d . . . H6 H 0.6066 0.0052 0.3287 0.053 Uiso 1 1 calc R . . C7 C 0.57003(13) 0.10790(19) 0.26294(17) 0.0446(7) Uani 1 1 d . . . H7 H 0.5890 0.1452 0.3049 0.054 Uiso 1 1 calc R . . C8 C 0.53201(13) 0.13514(19) 0.18535(18) 0.0452(7) Uani 1 1 d . . . C9 C 0.50038(13) 0.07438(18) 0.12184(18) 0.0417(7) Uani 1 1 d . . . C10 C 0.53971(12) 0.27989(17) 0.20504(15) 0.0340(6) Uani 1 1 d . . . C11 C 0.51444(14) 0.35565(19) 0.15636(17) 0.0448(7) Uani 1 1 d . . . C12 C 0.53313(15) 0.4377(2) 0.1939(2) 0.0509(8) Uani 1 1 d . . . H12 H 0.5606 0.4414 0.2486 0.061 Uiso 1 1 calc R . . C13 C 0.51147(12) 0.50611(19) 0.15123(18) 0.0426(7) Uani 1 1 d . . . H13 H 0.5246 0.5576 0.1748 0.051 Uiso 1 1 calc R . . C14 C 0.46598(14) 0.4983(2) 0.06518(18) 0.0479(7) Uani 1 1 d . . . C15 C 0.44111(12) 0.56851(18) 0.02088(17) 0.0394(6) Uani 1 1 d . . . H15 H 0.4532 0.6204 0.0438 0.047 Uiso 1 1 calc R . . C16 C 0.39694(13) 0.55931(19) -0.05999(19) 0.0463(7) Uani 1 1 d . . . H16 H 0.3793 0.6057 -0.0915 0.056 Uiso 1 1 calc R . . C17 C 0.37878(14) 0.47972(19) -0.09437(18) 0.0462(7) Uani 1 1 d . . . H17 H 0.3501 0.4746 -0.1485 0.055 Uiso 1 1 calc R . . C18 C 0.40275(12) 0.41085(18) -0.04920(16) 0.0391(6) Uani 1 1 d . . . H18 H 0.3890 0.3590 -0.0715 0.047 Uiso 1 1 calc R . . C19 C 0.45065(14) 0.41912(18) 0.03513(17) 0.0429(7) Uani 1 1 d . . . C20 C 0.54071(14) 0.23571(19) 0.04406(18) 0.0422(7) Uani 1 1 d . . . C21 C 0.42499(14) 0.22442(19) -0.06758(18) 0.0455(7) Uani 1 1 d . . . C22 C 0.38687(12) 0.22984(16) 0.03740(15) 0.0324(6) Uani 1 1 d . . . C23 C 0.29996(12) 0.40954(17) 0.12690(16) 0.0371(6) Uani 1 1 d . . . H23A H 0.3047 0.4559 0.1609 0.045 Uiso 1 1 calc R . . H23B H 0.3402 0.3916 0.1419 0.045 Uiso 1 1 calc R . . C24 C 0.26914(12) 0.44190(16) 0.04020(17) 0.0360(6) Uani 1 1 d . . . C25 C 0.23739(14) 0.38892(18) -0.09786(18) 0.0440(7) Uani 1 1 d . . . H25A H 0.2547 0.4362 -0.1091 0.053 Uiso 1 1 calc R . . H25B H 0.1954 0.4010 -0.1165 0.053 Uiso 1 1 calc R . . C26 C 0.24142(15) 0.31144(19) -0.14285(19) 0.0474(7) Uani 1 1 d . . . H26A H 0.2176 0.3203 -0.2001 0.057 Uiso 1 1 calc R . . H26B H 0.2830 0.3021 -0.1279 0.057 Uiso 1 1 calc R . . C27 C 0.22972(13) 0.16126(18) -0.14809(17) 0.0415(7) Uani 1 1 d . . . H27 H 0.2734 0.1519 -0.1189 0.050 Uiso 1 1 calc R . . C28 C 0.20629(14) 0.1555(2) -0.23832(17) 0.0472(7) Uani 1 1 d . . . H28A H 0.1670 0.1803 -0.2680 0.071 Uiso 1 1 calc R . . H28B H 0.2037 0.0988 -0.2534 0.071 Uiso 1 1 calc R . . H28C H 0.2336 0.1839 -0.2497 0.071 Uiso 1 1 calc R . . C29 C 0.20471(11) 0.47072(19) 0.00946(17) 0.0417(7) Uani 1 1 d . . . H29A H 0.1883 0.4940 -0.0429 0.063 Uiso 1 1 calc R . . H29B H 0.2048 0.5116 0.0450 0.063 Uiso 1 1 calc R . . H29C H 0.1804 0.4247 0.0069 0.063 Uiso 1 1 calc R . . C30 C 0.30711(14) 0.51408(19) 0.04046(19) 0.0490(8) Uani 1 1 d . . . H30A H 0.3481 0.4964 0.0620 0.074 Uiso 1 1 calc R . . H30B H 0.3060 0.5578 0.0727 0.074 Uiso 1 1 calc R . . H30C H 0.2911 0.5334 -0.0132 0.074 Uiso 1 1 calc R . . C31 C 0.59228(16) 0.7787(2) 0.3284(2) 0.0548(9) Uani 1 1 d . . . H31B H 0.6010 0.8345 0.3470 0.066 Uiso 1 1 calc R . . H31C H 0.5901 0.7453 0.3674 0.066 Uiso 1 1 calc R . . H31A H 0.5543 0.7766 0.2788 0.066 Uiso 1 1 calc R . . C32 C 0.64259(16) 0.6625(2) 0.2952(2) 0.0579(9) Uani 1 1 d . . . H32A H 0.6147 0.6306 0.3028 0.087 Uiso 1 1 calc R . . H32C H 0.6827 0.6411 0.3286 0.087 Uiso 1 1 calc R . . H32B H 0.6316 0.6595 0.2403 0.087 Uiso 1 1 calc R . . C33 C 0.68887(16) 0.8021(2) 0.3308(2) 0.0587(9) Uani 1 1 d . . . H33 H 0.7208 0.7863 0.3245 0.070 Uiso 1 1 calc R . . Fe1 Fe 0.465713(18) 0.23213(2) 0.04685(2) 0.03317(12) Uani 1 1 d . . . N1 N 0.46583(12) 0.10606(15) 0.04787(15) 0.0461(6) Uani 1 1 d . . . N2 N 0.51640(11) 0.21271(15) 0.16124(14) 0.0409(6) Uani 1 1 d . . . N3 N 0.47532(11) 0.34875(15) 0.07762(15) 0.0433(6) Uani 1 1 d . . . N4 N 0.58658(12) 0.23752(17) 0.04815(16) 0.0476(6) Uani 1 1 d . . . N5 N 0.40070(12) 0.21859(16) -0.13687(16) 0.0520(7) Uani 1 1 d . . . N6 N 0.33900(11) 0.22568(16) 0.02749(15) 0.0436(6) Uani 1 1 d . . . N7 N 0.27024(10) 0.37332(14) -0.01140(14) 0.0387(5) Uani 1 1 d . . . H7B H 0.3096 0.3713 0.0021 0.046 Uiso 1 1 calc R . . N8 N 0.21838(11) 0.23984(14) -0.12105(14) 0.0361(5) Uani 1 1 d . . . H8A H 0.1776 0.2458 -0.1468 0.043 Uiso 1 1 calc R . . N9 N 0.64078(14) 0.74713(17) 0.31621(17) 0.0582(8) Uani 1 1 d . . . Ni1 Ni 0.2500 0.2500 0.0000 0.03457(14) Uani 1 2 d S . . O1 O 0.57658(9) 0.28893(12) 0.27679(11) 0.0425(5) Uani 1 1 d . . . O2 O 0.68447(10) 0.87473(14) 0.35303(13) 0.0542(6) Uani 1 1 d . . . O1W O 0.18383(18) 0.4891(3) 0.7053(2) 0.0481(10) Uani 0.50 1 d P . . H1X H 0.1800 0.5411 0.7001 0.058 Uiso 0.50 1 d PR . . H1Y H 0.1503 0.4678 0.6940 0.058 Uiso 0.50 1 d PR . . O2W O 0.19032(19) 0.3124(3) 0.5619(3) 0.0535(11) Uani 0.50 1 d P . . H2X H 0.1891 0.3494 0.5918 0.064 Uiso 0.50 1 d PR . . H2Y H 0.1749 0.3310 0.5146 0.064 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0315(14) 0.0405(16) 0.0419(16) 0.0035(12) 0.0092(12) -0.0004(12) C2 0.0401(16) 0.0431(16) 0.0462(17) -0.0137(13) 0.0111(13) -0.0009(14) C3 0.0428(17) 0.0399(16) 0.0488(18) 0.0032(13) 0.0137(14) 0.0013(14) C4 0.0469(17) 0.0404(16) 0.0530(19) -0.0001(14) 0.0192(15) -0.0043(14) C5 0.0406(16) 0.0412(16) 0.0498(18) 0.0082(13) 0.0151(14) 0.0061(14) C6 0.0373(15) 0.0432(16) 0.0440(16) 0.0075(13) 0.0155(13) -0.0002(13) C7 0.0392(16) 0.0472(17) 0.0365(15) -0.0121(13) 0.0117(13) -0.0087(13) C8 0.0314(14) 0.0490(17) 0.0416(16) 0.0032(14) 0.0091(12) 0.0135(13) C9 0.0358(15) 0.0380(15) 0.0422(16) 0.0018(12) 0.0136(13) -0.0002(12) C10 0.0305(13) 0.0357(14) 0.0288(13) -0.0029(10) 0.0103(11) -0.0031(11) C11 0.0408(16) 0.0452(17) 0.0358(15) -0.0020(12) 0.0107(13) 0.0017(13) C12 0.0460(17) 0.0475(17) 0.0421(16) -0.0137(14) 0.0106(14) -0.0134(15) C13 0.0336(15) 0.0429(16) 0.0476(17) -0.0118(13) 0.0182(13) -0.0093(13) C14 0.0425(17) 0.0442(17) 0.0433(18) -0.0055(13) 0.0124(14) -0.0035(14) C15 0.0303(14) 0.0387(15) 0.0424(15) -0.0089(12) 0.0138(12) -0.0048(12) C16 0.0329(15) 0.0442(16) 0.0483(17) 0.0024(13) 0.0115(13) -0.0078(13) C17 0.0439(17) 0.0450(17) 0.0361(15) -0.0047(13) 0.0108(13) -0.0032(14) C18 0.0321(14) 0.0409(15) 0.0339(14) -0.0113(12) 0.0096(12) -0.0030(12) C19 0.0416(16) 0.0372(15) 0.0395(16) 0.0044(12) 0.0136(13) -0.0010(13) C20 0.0373(16) 0.0421(15) 0.0416(16) -0.0077(12) 0.0163(13) -0.0078(13) C21 0.0461(17) 0.0427(16) 0.0389(16) -0.0082(13) 0.0158(14) 0.0133(14) C22 0.0307(14) 0.0289(13) 0.0296(13) -0.0069(10) 0.0099(11) -0.0023(11) C23 0.0284(13) 0.0381(14) 0.0385(15) -0.0146(12) 0.0128(11) -0.0016(12) C24 0.0292(13) 0.0282(13) 0.0407(15) -0.0065(11) 0.0110(11) 0.0029(11) C25 0.0411(16) 0.0366(15) 0.0437(16) -0.0027(12) 0.0142(13) 0.0008(13) C26 0.0452(17) 0.0453(17) 0.0428(17) -0.0043(13) 0.0165(14) -0.0091(14) C27 0.0337(14) 0.0461(16) 0.0364(15) -0.0122(12) 0.0123(12) 0.0023(13) C28 0.0421(17) 0.0468(17) 0.0428(17) -0.0076(13) 0.0150(14) 0.0085(14) C29 0.0244(13) 0.0479(16) 0.0436(16) -0.0039(13) 0.0110(12) 0.0108(12) C30 0.0446(17) 0.0397(16) 0.0489(18) -0.0142(13) 0.0143(14) -0.0129(14) C31 0.062(2) 0.0461(18) 0.0432(18) 0.0167(14) 0.0176(16) 0.0163(16) C32 0.054(2) 0.055(2) 0.054(2) -0.0142(16) 0.0203(16) -0.0239(17) C33 0.0494(19) 0.0445(18) 0.060(2) 0.0122(15) 0.0124(16) 0.0128(16) Fe1 0.0322(2) 0.0333(2) 0.0308(2) -0.00277(15) 0.01395(17) -0.00498(16) N1 0.0462(14) 0.0378(13) 0.0449(14) -0.0019(11) 0.0168(12) -0.0011(11) N2 0.0371(13) 0.0421(13) 0.0354(13) -0.0080(10) 0.0129(10) -0.0053(11) N3 0.0367(13) 0.0393(13) 0.0407(13) -0.0041(11) 0.0106(11) 0.0008(11) N4 0.0381(14) 0.0521(15) 0.0485(15) -0.0166(12) 0.0195(12) -0.0072(12) N5 0.0477(15) 0.0469(15) 0.0469(16) -0.0176(12) 0.0140(13) 0.0166(12) N6 0.0318(13) 0.0419(14) 0.0431(14) -0.0083(11) 0.0093(11) -0.0015(11) N7 0.0307(12) 0.0352(12) 0.0481(14) -0.0093(10) 0.0189(11) -0.0086(10) N8 0.0292(11) 0.0415(13) 0.0336(12) -0.0054(10) 0.0133(10) -0.0036(10) N9 0.0579(18) 0.0506(16) 0.0471(16) -0.0095(12) 0.0136(14) 0.0024(14) Ni1 0.0293(3) 0.0311(3) 0.0366(3) -0.00486(19) 0.0122(2) 0.00003(19) O1 0.0386(11) 0.0434(11) 0.0279(10) -0.0027(8) 0.0048(8) -0.0143(9) O2 0.0514(13) 0.0523(13) 0.0464(13) 0.0201(10) 0.0162(10) 0.0213(11) O1W 0.046(2) 0.046(2) 0.040(2) -0.0098(18) 0.0141(19) -0.018(2) O2W 0.044(2) 0.051(3) 0.049(3) 0.015(2) 0.013(2) 0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.362(4) . ? C1 C2 1.438(4) . ? C1 H1 0.9300 . ? C2 C3 1.362(4) . ? C2 H2 0.9300 . ? C3 C4 1.450(4) . ? C3 H3 0.9300 . ? C4 C5 1.370(4) . ? C4 C9 1.422(4) . ? C5 C6 1.435(4) . ? C5 H5 0.9300 . ? C6 C7 1.402(4) . ? C6 H6 0.9300 . ? C7 C8 1.387(4) . ? C7 H7 0.9300 . ? C8 N2 1.333(4) . ? C8 C9 1.462(4) . ? C9 N1 1.349(4) . ? C10 O1 1.232(3) . ? C10 N2 1.325(3) . ? C10 C11 1.485(4) . ? C11 N3 1.341(4) . ? C11 C12 1.477(4) . ? C12 C13 1.328(5) . ? C12 H12 0.9300 . ? C13 C14 1.479(4) . ? C13 H13 0.9300 . ? C14 C15 1.375(4) . ? C14 C19 1.384(4) . ? C15 C16 1.401(4) . ? C15 H15 0.9300 . ? C16 C17 1.421(4) . ? C16 H16 0.9300 . ? C17 C18 1.360(4) . ? C17 H17 0.9300 . ? C18 C19 1.470(4) . ? C18 H18 0.9300 . ? C19 N3 1.363(4) . ? C20 N4 1.147(4) . ? C20 Fe1 1.968(3) . ? C21 N5 1.166(4) . ? C21 Fe1 1.922(3) . ? C22 N6 1.151(4) . ? C22 Fe1 1.950(3) . ? C23 C24 1.546(4) . ? C23 C27 1.553(4) 7 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N7 1.513(3) . ? C24 C29 1.524(4) . ? C24 C30 1.528(4) . ? C25 N7 1.470(4) . ? C25 C26 1.569(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 N8 1.467(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N8 1.468(4) . ? C27 C28 1.544(4) . ? C27 C23 1.553(4) 7 ? C27 H27 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N9 1.483(5) . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C31 H31A 0.9600 . ? C32 N9 1.442(4) . ? C32 H32A 0.9600 . ? C32 H32C 0.9600 . ? C32 H32B 0.9600 . ? C33 O2 1.283(4) . ? C33 N9 1.435(5) . ? C33 H33 0.9300 . ? Fe1 N2 1.947(2) . ? Fe1 N3 1.964(2) . ? Fe1 N1 2.048(3) . ? N6 Ni1 2.112(3) . ? N7 Ni1 2.111(2) . ? N7 H7B 0.9100 . ? N8 Ni1 2.073(2) . ? N8 H8A 0.9100 . ? Ni1 N8 2.073(2) 7 ? Ni1 N7 2.111(2) 7 ? Ni1 N6 2.112(3) 7 ? O1W H1X 0.8501 . ? O1W H1Y 0.8500 . ? O2W H2X 0.8500 . ? O2W H2Y 0.8501 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 118.2(3) . . ? N1 C1 H1 120.9 . . ? C2 C1 H1 120.9 . . ? C3 C2 C1 123.5(3) . . ? C3 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? C2 C3 C4 117.8(3) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C9 120.2(3) . . ? C5 C4 C3 123.6(3) . . ? C9 C4 C3 116.0(3) . . ? C4 C5 C6 118.5(3) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 123.0(3) . . ? C7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C8 C7 C6 118.8(3) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? N2 C8 C7 127.1(3) . . ? N2 C8 C9 113.8(2) . . ? C7 C8 C9 118.9(3) . . ? N1 C9 C4 124.4(3) . . ? N1 C9 C8 115.0(3) . . ? C4 C9 C8 120.4(3) . . ? O1 C10 N2 131.4(3) . . ? O1 C10 C11 117.2(2) . . ? N2 C10 C11 111.5(2) . . ? N3 C11 C12 120.4(3) . . ? N3 C11 C10 119.2(3) . . ? C12 C11 C10 120.4(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 118.2(3) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C15 C14 C19 124.4(3) . . ? C15 C14 C13 118.9(3) . . ? C19 C14 C13 116.6(3) . . ? C14 C15 C16 117.8(3) . . ? C14 C15 H15 121.1 . . ? C16 C15 H15 121.1 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.4(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? N3 C19 C14 125.4(3) . . ? N3 C19 C18 117.7(3) . . ? C14 C19 C18 116.9(3) . . ? N4 C20 Fe1 175.2(3) . . ? N5 C21 Fe1 179.0(3) . . ? N6 C22 Fe1 175.7(2) . . ? C24 C23 C27 119.9(2) . 7 ? C24 C23 H23A 107.4 . . ? C27 C23 H23A 107.4 7 . ? C24 C23 H23B 107.3 . . ? C27 C23 H23B 107.4 7 . ? H23A C23 H23B 106.9 . . ? N7 C24 C29 110.9(2) . . ? N7 C24 C30 109.5(2) . . ? C29 C24 C30 109.6(2) . . ? N7 C24 C23 107.7(2) . . ? C29 C24 C23 112.1(2) . . ? C30 C24 C23 106.9(2) . . ? N7 C25 C26 109.9(2) . . ? N7 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? N7 C25 H25B 109.7 . . ? C26 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? N8 C26 C25 108.6(3) . . ? N8 C26 H26A 110.0 . . ? C25 C26 H26A 110.0 . . ? N8 C26 H26B 110.0 . . ? C25 C26 H26B 110.0 . . ? H26A C26 H26B 108.4 . . ? N8 C27 C28 115.5(2) . . ? N8 C27 C23 109.3(2) . 7 ? C28 C27 C23 107.7(2) . 7 ? N8 C27 H27 108.1 . . ? C28 C27 H27 108.1 . . ? C23 C27 H27 108.1 7 . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C24 C30 H30A 109.5 . . ? C24 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C24 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N9 C31 H31B 109.5 . . ? N9 C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N9 C31 H31A 109.5 . . ? H31B C31 H31A 109.5 . . ? H31C C31 H31A 109.5 . . ? N9 C32 H32A 109.5 . . ? N9 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? N9 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? H32C C32 H32B 109.5 . . ? O2 C33 N9 114.8(3) . . ? O2 C33 H33 122.6 . . ? N9 C33 H33 122.6 . . ? C21 Fe1 N2 164.85(11) . . ? C21 Fe1 C22 88.31(13) . . ? N2 Fe1 C22 99.02(11) . . ? C21 Fe1 N3 109.01(12) . . ? N2 Fe1 N3 84.32(10) . . ? C22 Fe1 N3 90.47(11) . . ? C21 Fe1 C20 85.72(13) . . ? N2 Fe1 C20 87.01(12) . . ? C22 Fe1 C20 173.95(11) . . ? N3 Fe1 C20 90.54(12) . . ? C21 Fe1 N1 86.75(12) . . ? N2 Fe1 N1 80.21(10) . . ? C22 Fe1 N1 88.74(11) . . ? N3 Fe1 N1 164.19(11) . . ? C20 Fe1 N1 91.90(12) . . ? C9 N1 C1 119.6(3) . . ? C9 N1 Fe1 112.88(19) . . ? C1 N1 Fe1 127.1(2) . . ? C10 N2 C8 126.6(2) . . ? C10 N2 Fe1 114.9(2) . . ? C8 N2 Fe1 117.44(19) . . ? C11 N3 C19 117.9(3) . . ? C11 N3 Fe1 109.5(2) . . ? C19 N3 Fe1 132.6(2) . . ? C22 N6 Ni1 165.2(2) . . ? C25 N7 C24 116.2(2) . . ? C25 N7 Ni1 104.92(16) . . ? C24 N7 Ni1 122.51(18) . . ? C25 N7 H7B 103.6 . . ? C24 N7 H7B 103.6 . . ? Ni1 N7 H7B 103.6 . . ? C26 N8 C27 113.5(2) . . ? C26 N8 Ni1 106.76(17) . . ? C27 N8 Ni1 116.47(18) . . ? C26 N8 H8A 106.5 . . ? C27 N8 H8A 106.5 . . ? Ni1 N8 H8A 106.5 . . ? C33 N9 C32 119.8(3) . . ? C33 N9 C31 118.1(3) . . ? C32 N9 C31 121.9(3) . . ? N8 Ni1 N8 180.0 7 . ? N8 Ni1 N7 94.11(9) 7 . ? N8 Ni1 N7 85.89(9) . . ? N8 Ni1 N7 85.89(9) 7 7 ? N8 Ni1 N7 94.11(9) . 7 ? N7 Ni1 N7 180.0 . 7 ? N8 Ni1 N6 90.66(10) 7 7 ? N8 Ni1 N6 89.34(10) . 7 ? N7 Ni1 N6 95.30(9) . 7 ? N7 Ni1 N6 84.70(9) 7 7 ? N8 Ni1 N6 89.34(10) 7 . ? N8 Ni1 N6 90.66(10) . . ? N7 Ni1 N6 84.70(9) . . ? N7 Ni1 N6 95.30(9) 7 . ? N6 Ni1 N6 180.0 7 . ? H1X O1W H1Y 109.5 . . ? H2X O2W H2Y 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.4(5) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 C5 179.5(3) . . . . ? C2 C3 C4 C9 3.6(5) . . . . ? C9 C4 C5 C6 0.2(5) . . . . ? C3 C4 C5 C6 -175.5(3) . . . . ? C4 C5 C6 C7 1.8(5) . . . . ? C5 C6 C7 C8 -3.7(5) . . . . ? C6 C7 C8 N2 177.6(3) . . . . ? C6 C7 C8 C9 3.4(5) . . . . ? C5 C4 C9 N1 175.8(3) . . . . ? C3 C4 C9 N1 -8.2(5) . . . . ? C5 C4 C9 C8 -0.3(5) . . . . ? C3 C4 C9 C8 175.7(3) . . . . ? N2 C8 C9 N1 7.0(4) . . . . ? C7 C8 C9 N1 -178.0(3) . . . . ? N2 C8 C9 C4 -176.5(3) . . . . ? C7 C8 C9 C4 -1.5(5) . . . . ? O1 C10 C11 N3 178.3(3) . . . . ? N2 C10 C11 N3 -2.8(4) . . . . ? O1 C10 C11 C12 -0.5(4) . . . . ? N2 C10 C11 C12 178.4(3) . . . . ? N3 C11 C12 C13 0.6(5) . . . . ? C10 C11 C12 C13 179.3(3) . . . . ? C11 C12 C13 C14 2.5(5) . . . . ? C12 C13 C14 C15 177.1(3) . . . . ? C12 C13 C14 C19 -1.8(5) . . . . ? C19 C14 C15 C16 0.5(5) . . . . ? C13 C14 C15 C16 -178.3(3) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? C15 C16 C17 C18 1.6(5) . . . . ? C16 C17 C18 C19 -3.7(5) . . . . ? C15 C14 C19 N3 179.0(3) . . . . ? C13 C14 C19 N3 -2.2(5) . . . . ? C15 C14 C19 C18 -2.5(5) . . . . ? C13 C14 C19 C18 176.3(3) . . . . ? C17 C18 C19 N3 -177.3(3) . . . . ? C17 C18 C19 C14 4.1(5) . . . . ? C27 C23 C24 N7 -65.9(3) 7 . . . ? C27 C23 C24 C29 56.4(3) 7 . . . ? C27 C23 C24 C30 176.5(2) 7 . . . ? N7 C25 C26 N8 56.0(3) . . . . ? C4 C9 N1 C1 9.2(5) . . . . ? C8 C9 N1 C1 -174.5(3) . . . . ? C4 C9 N1 Fe1 -178.2(3) . . . . ? C8 C9 N1 Fe1 -1.9(3) . . . . ? C2 C1 N1 C9 -5.4(5) . . . . ? C2 C1 N1 Fe1 -176.8(2) . . . . ? C21 Fe1 N1 C9 170.1(2) . . . . ? N2 Fe1 N1 C9 -2.2(2) . . . . ? C22 Fe1 N1 C9 -101.5(2) . . . . ? N3 Fe1 N1 C9 -14.3(5) . . . . ? C20 Fe1 N1 C9 84.5(2) . . . . ? C21 Fe1 N1 C1 -18.0(3) . . . . ? N2 Fe1 N1 C1 169.7(3) . . . . ? C22 Fe1 N1 C1 70.4(3) . . . . ? N3 Fe1 N1 C1 157.6(3) . . . . ? C20 Fe1 N1 C1 -103.6(3) . . . . ? O1 C10 N2 C8 -5.8(5) . . . . ? C11 C10 N2 C8 175.6(3) . . . . ? O1 C10 N2 Fe1 -173.7(3) . . . . ? C11 C10 N2 Fe1 7.7(3) . . . . ? C7 C8 N2 C10 8.8(5) . . . . ? C9 C8 N2 C10 -176.7(3) . . . . ? C7 C8 N2 Fe1 176.4(3) . . . . ? C9 C8 N2 Fe1 -9.1(4) . . . . ? C21 Fe1 N2 C10 144.4(5) . . . . ? C22 Fe1 N2 C10 -97.4(2) . . . . ? N3 Fe1 N2 C10 -7.8(2) . . . . ? C20 Fe1 N2 C10 83.0(2) . . . . ? N1 Fe1 N2 C10 175.5(2) . . . . ? C21 Fe1 N2 C8 -24.6(6) . . . . ? C22 Fe1 N2 C8 93.5(2) . . . . ? N3 Fe1 N2 C8 -176.9(2) . . . . ? C20 Fe1 N2 C8 -86.1(2) . . . . ? N1 Fe1 N2 C8 6.4(2) . . . . ? C12 C11 N3 C19 -4.3(5) . . . . ? C10 C11 N3 C19 176.9(3) . . . . ? C12 C11 N3 Fe1 175.5(2) . . . . ? C10 C11 N3 Fe1 -3.3(4) . . . . ? C14 C19 N3 C11 5.3(5) . . . . ? C18 C19 N3 C11 -173.2(3) . . . . ? C14 C19 N3 Fe1 -174.5(3) . . . . ? C18 C19 N3 Fe1 7.0(5) . . . . ? C21 Fe1 N3 C11 -166.9(2) . . . . ? N2 Fe1 N3 C11 5.7(2) . . . . ? C22 Fe1 N3 C11 104.7(2) . . . . ? C20 Fe1 N3 C11 -81.2(2) . . . . ? N1 Fe1 N3 C11 17.7(5) . . . . ? C21 Fe1 N3 C19 12.9(3) . . . . ? N2 Fe1 N3 C19 -174.5(3) . . . . ? C22 Fe1 N3 C19 -75.5(3) . . . . ? C20 Fe1 N3 C19 98.6(3) . . . . ? N1 Fe1 N3 C19 -162.5(4) . . . . ? C26 C25 N7 C24 -178.5(2) . . . . ? C26 C25 N7 Ni1 -39.8(3) . . . . ? C29 C24 N7 C25 50.9(3) . . . . ? C30 C24 N7 C25 -70.2(3) . . . . ? C23 C24 N7 C25 173.9(2) . . . . ? C29 C24 N7 Ni1 -79.9(3) . . . . ? C30 C24 N7 Ni1 159.05(19) . . . . ? C23 C24 N7 Ni1 43.1(3) . . . . ? C25 C26 N8 C27 -169.8(2) . . . . ? C25 C26 N8 Ni1 -40.1(3) . . . . ? C28 C27 N8 C26 -54.8(3) . . . . ? C23 C27 N8 C26 -176.4(2) 7 . . . ? C28 C27 N8 Ni1 -179.43(19) . . . . ? C23 C27 N8 Ni1 59.0(3) 7 . . . ? O2 C33 N9 C32 -176.5(3) . . . . ? O2 C33 N9 C31 -0.3(4) . . . . ? C26 N8 Ni1 N7 15.02(19) . . . . ? C27 N8 Ni1 N7 143.0(2) . . . . ? C26 N8 Ni1 N7 -164.98(19) . . . 7 ? C27 N8 Ni1 N7 -37.0(2) . . . 7 ? C26 N8 Ni1 N6 110.4(2) . . . 7 ? C27 N8 Ni1 N6 -121.7(2) . . . 7 ? C26 N8 Ni1 N6 -69.6(2) . . . . ? C27 N8 Ni1 N6 58.3(2) . . . . ? C25 N7 Ni1 N8 -165.65(18) . . . 7 ? C24 N7 Ni1 N8 -30.3(2) . . . 7 ? C25 N7 Ni1 N8 14.36(18) . . . . ? C24 N7 Ni1 N8 149.7(2) . . . . ? C25 N7 Ni1 N6 -74.60(19) . . . 7 ? C24 N7 Ni1 N6 60.7(2) . . . 7 ? C25 N7 Ni1 N6 105.40(19) . . . . ? C24 N7 Ni1 N6 -119.3(2) . . . . ? C22 N6 Ni1 N8 -103.1(9) . . . 7 ? C22 N6 Ni1 N8 76.9(9) . . . . ? C22 N6 Ni1 N7 -8.9(9) . . . . ? C22 N6 Ni1 N7 171.1(9) . . . 7 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.249 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 948659' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H63.22 Cu Fe2 N18 O2, 0.61(O)' _chemical_formula_sum 'C60 H63.22 Cu Fe2 N18 O2.61' _chemical_formula_weight 1253.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.283(2) _cell_length_b 12.391(3) _cell_length_c 13.032(3) _cell_angle_alpha 107.05(3) _cell_angle_beta 94.67(3) _cell_angle_gamma 94.81(3) _cell_volume 1572.2(5) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5025 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 649.8 _exptl_absorpt_coefficient_mu 0.851 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8284 _exptl_absorpt_correction_T_max 0.8619 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13145 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5466 _reflns_number_gt 4611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The restraints that were used for the refinement of the disordered n-butyl group (C28,C29,C30) are: isor 0.01 c29' C30' dfix 1.5 0.005 C29' C30' C28' C29' C27 C28' dfix 2.5 0.005 C28' C30' The water O1w is not present with unit occupancy,and so it is allowed a free variable refinement with partial occupancy ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+9.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5466 _refine_ls_number_parameters 388 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1525 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8129(5) 0.9542(4) 0.6049(4) 0.0303(11) Uani 1 1 d . . . C2 C 0.7514(5) 0.7575(5) 0.6232(5) 0.0398(13) Uani 1 1 d . . . C3 C 1.0720(5) 0.9687(5) 0.6918(4) 0.0322(12) Uani 1 1 d . . . C4 C 0.8442(6) 0.9962(7) 0.8805(5) 0.0545(18) Uani 1 1 d . . . C5 C 0.8409(6) 1.0935(6) 0.8477(5) 0.0524(17) Uani 1 1 d . . . H5 H 0.8675 1.0926 0.7794 0.063 Uiso 1 1 calc R . . C6 C 0.8000(6) 1.1905(7) 0.9123(6) 0.073(2) Uani 1 1 d . . . H6 H 0.7986 1.2567 0.8897 0.087 Uiso 1 1 calc R . . C7 C 0.7594(8) 1.1896(10) 1.0148(7) 0.093(3) Uani 1 1 d . . . H7 H 0.7287 1.2554 1.0598 0.112 Uiso 1 1 calc R . . C8 C 0.7640(9) 1.0973(11) 1.0479(7) 0.100(4) Uani 1 1 d . . . H8 H 0.7374 1.0988 1.1163 0.120 Uiso 1 1 calc R . . C9 C 0.8071(7) 0.9996(8) 0.9835(5) 0.071(2) Uani 1 1 d . . . C10 C 0.8187(9) 0.9062(11) 1.0206(6) 0.096(4) Uani 1 1 d . . . H10 H 0.7902 0.9062 1.0882 0.115 Uiso 1 1 calc R . . C11 C 0.8707(8) 0.8157(9) 0.9603(7) 0.087(3) Uani 1 1 d . . . H11 H 0.8827 0.7529 0.9866 0.105 Uiso 1 1 calc R . . C12 C 0.9074(7) 0.8143(7) 0.8573(5) 0.060(2) Uani 1 1 d . . . C13 C 0.9747(7) 0.7203(6) 0.7907(6) 0.062(2) Uani 1 1 d . . . C14 C 1.0689(6) 0.6715(5) 0.6194(6) 0.0504(17) Uani 1 1 d . . . C15 C 1.1462(6) 0.5879(6) 0.6293(7) 0.065(2) Uani 1 1 d . . . H15 H 1.1622 0.5737 0.6968 0.078 Uiso 1 1 calc R . . C16 C 1.2000(7) 0.5252(6) 0.5392(9) 0.079(3) Uani 1 1 d . . . H16 H 1.2540 0.4686 0.5464 0.095 Uiso 1 1 calc R . . C17 C 1.1778(6) 0.5422(5) 0.4414(8) 0.070(2) Uani 1 1 d . . . H17 H 1.2143 0.4962 0.3812 0.084 Uiso 1 1 calc R . . C18 C 1.0999(6) 0.6287(5) 0.4277(6) 0.0515(17) Uani 1 1 d . . . C19 C 1.0698(6) 0.6523(5) 0.3317(6) 0.0567(18) Uani 1 1 d . . . H19 H 1.1004 0.6086 0.2673 0.068 Uiso 1 1 calc R . . C20 C 0.9960(6) 0.7384(5) 0.3293(5) 0.0473(15) Uani 1 1 d . . . H20 H 0.9751 0.7548 0.2635 0.057 Uiso 1 1 calc R . . C21 C 0.9515(5) 0.8026(5) 0.4253(5) 0.0386(13) Uani 1 1 d . . . H21 H 0.9029 0.8640 0.4235 0.046 Uiso 1 1 calc R . . C22 C 1.0492(5) 0.6935(5) 0.5198(5) 0.0440(15) Uani 1 1 d . . . C23 C 0.4426(6) 0.9215(5) 0.6751(5) 0.0439(15) Uani 1 1 d . . . H23A H 0.3884 0.9224 0.7346 0.053 Uiso 1 1 calc R . . H23B H 0.5337 0.9118 0.6986 0.053 Uiso 1 1 calc R . . C24 C 0.3887(6) 0.8261(5) 0.5758(5) 0.0460(15) Uani 1 1 d . . . H24A H 0.3944 0.7520 0.5893 0.055 Uiso 1 1 calc R . . H24B H 0.2955 0.8325 0.5552 0.055 Uiso 1 1 calc R . . C25 C 0.4081(6) 0.7612(5) 0.3795(5) 0.0464(15) Uani 1 1 d . . . H25A H 0.3969 0.6814 0.3805 0.056 Uiso 1 1 calc R . . H25B H 0.3197 0.7833 0.3652 0.056 Uiso 1 1 calc R . . C26 C 0.4876(6) 0.8723(5) 0.2672(5) 0.0455(15) Uani 1 1 d . . . H26A H 0.3965 0.8889 0.2531 0.055 Uiso 1 1 calc R . . H26B H 0.5293 0.8629 0.1997 0.055 Uiso 1 1 calc R . . C27 C 0.6084(6) 0.7161(6) 0.2880(6) 0.0593(18) Uani 1 1 d D . . H27A H 0.6510 0.7268 0.2257 0.071 Uiso 0.664(8) 1 calc PR A 1 H27B H 0.6678 0.7565 0.3543 0.071 Uiso 0.664(8) 1 calc PR A 1 H27C H 0.5894 0.6825 0.3234 0.071 Uiso 0.336(8) 1 d PR A 2 H27D H 0.6609 0.7933 0.3091 0.071 Uiso 0.336(8) 1 d PR A 2 C28 C 0.5920(11) 0.5960(10) 0.2779(12) 0.081(4) Uani 0.664(8) 1 d P A 1 H28A H 0.5581 0.5861 0.3440 0.097 Uiso 0.664(8) 1 calc PR A 1 H28B H 0.6790 0.5673 0.2734 0.097 Uiso 0.664(8) 1 calc PR A 1 C28' C 0.642(2) 0.661(2) 0.1749(10) 0.112(12) Uani 0.336(8) 1 d PD A 2 H28C H 0.5581 0.6287 0.1284 0.135 Uiso 0.336(8) 1 calc PR A 2 H28D H 0.6816 0.7218 0.1483 0.135 Uiso 0.336(8) 1 calc PR A 2 C29 C 0.4999(17) 0.5252(11) 0.1808(14) 0.123(7) Uani 0.664(8) 1 d P A 1 H29A H 0.5340 0.5330 0.1142 0.147 Uiso 0.664(8) 1 calc PR A 1 H29B H 0.4126 0.5533 0.1845 0.147 Uiso 0.664(8) 1 calc PR A 1 C29' C 0.731(2) 0.5695(19) 0.1580(12) 0.101(9) Uani 0.336(8) 1 d PDU A 2 H29C H 0.8012 0.5903 0.2195 0.121 Uiso 0.336(8) 1 calc PR A 2 H29D H 0.6805 0.4979 0.1580 0.121 Uiso 0.336(8) 1 calc PR A 2 C30 C 0.4857(3) 0.39493(8) 0.17615(17) 0.140(7) Uani 0.664(8) 1 d P A 1 H30A H 0.5688 0.3764 0.2053 0.210 Uiso 0.664(8) 1 calc PR A 1 H30B H 0.4633 0.3474 0.1010 0.210 Uiso 0.664(8) 1 calc PR A 1 H30C H 0.4160 0.3808 0.2192 0.210 Uiso 0.664(8) 1 calc PR A 1 C30' C 0.7937(6) 0.54898(7) 0.05525(15) 0.120(11) Uani 0.336(8) 1 d PRDU A 2 H30G H 0.7362 0.5096 -0.0055 0.180 Uiso 0.336(8) 1 d PR A 2 H30D H 0.8727 0.5052 0.0605 0.180 Uiso 0.336(8) 1 d PR A 2 H30F H 0.8316 0.6242 0.0518 0.180 Uiso 0.336(8) 1 d PR A 2 Cu1 Cu 0.50000(10) 1.00000(9) 0.5000(2) 0.0353(3) Uani 1 2 d SR . . Fe1 Fe 0.91909(6) 0.85501(6) 0.66008(6) 0.0353(2) Uani 1 1 d R . . N1 N 0.74226(8) 1.00372(6) 0.56811(8) 0.0378(11) Uani 1 1 d R . . N2 N 0.65248(9) 0.70084(7) 0.59840(12) 0.0533(14) Uani 1 1 d R . . N3 N 1.16473(9) 1.03377(7) 0.70995(9) 0.0373(11) Uani 1 1 d R . . N4 N 0.88772(8) 0.89940(6) 0.81645(7) 0.0466(13) Uani 1 1 d R . . N5 N 1.00527(7) 0.74192(6) 0.69933(7) 0.0440(12) Uani 1 1 d R . . N6 N 0.97471(10) 0.78059(7) 0.51699(10) 0.0343(10) Uani 1 1 d R . . N7 N 0.44000(10) 1.02864(10) 0.6473(3) 0.0366(11) Uani 1 1 d R . . H7A H 0.3527 1.0424 0.6412 0.044 Uiso 1 1 d R . . N8 N 0.4690(4) 0.8350(4) 0.4882(4) 0.0370(11) Uani 1 1 d . . . H8A H 0.5500 0.8107 0.5018 0.044 Uiso 1 1 d R . . N9 N 0.4832(4) 0.7677(4) 0.2927(4) 0.0450(12) Uani 1 1 d . A . O1 O 0.9990(6) 0.6376(4) 0.8201(4) 0.0888(19) Uani 1 1 d . . . O1W O 0.4971(16) 0.5056(17) 0.4077(19) 0.099(10) Uani 0.303(17) 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(3) 0.036(3) 0.030(3) 0.011(2) 0.005(2) 0.000(2) C2 0.034(3) 0.046(3) 0.047(3) 0.025(3) 0.003(3) 0.009(3) C3 0.028(3) 0.044(3) 0.028(3) 0.014(2) 0.004(2) 0.011(2) C4 0.025(3) 0.096(6) 0.034(3) 0.013(4) -0.002(3) -0.011(3) C5 0.029(3) 0.082(5) 0.037(3) 0.002(3) 0.002(3) 0.010(3) C6 0.040(4) 0.091(6) 0.062(5) -0.014(4) -0.007(3) 0.012(4) C7 0.042(4) 0.151(10) 0.049(5) -0.026(6) 0.010(4) 0.005(5) C8 0.056(5) 0.175(11) 0.044(5) 0.004(6) 0.011(4) -0.030(6) C9 0.048(4) 0.119(7) 0.032(4) 0.012(4) 0.005(3) -0.024(4) C10 0.070(6) 0.170(11) 0.035(4) 0.032(6) -0.002(4) -0.053(6) C11 0.075(6) 0.134(8) 0.057(5) 0.062(6) -0.029(4) -0.052(6) C12 0.048(4) 0.088(5) 0.046(4) 0.040(4) -0.015(3) -0.027(4) C13 0.053(4) 0.070(5) 0.067(5) 0.044(4) -0.025(4) -0.023(4) C14 0.028(3) 0.039(3) 0.086(5) 0.029(3) -0.012(3) -0.005(3) C15 0.042(4) 0.039(4) 0.113(7) 0.032(4) -0.023(4) -0.001(3) C16 0.044(4) 0.031(4) 0.156(9) 0.029(5) -0.025(5) -0.001(3) C17 0.035(4) 0.033(4) 0.131(8) 0.008(4) 0.006(4) 0.003(3) C18 0.030(3) 0.028(3) 0.084(5) 0.002(3) 0.000(3) -0.005(2) C19 0.040(4) 0.043(4) 0.073(5) -0.004(3) 0.016(3) -0.004(3) C20 0.047(4) 0.046(4) 0.042(3) 0.004(3) 0.009(3) -0.001(3) C21 0.033(3) 0.038(3) 0.046(3) 0.014(3) 0.006(3) 0.003(2) C22 0.026(3) 0.033(3) 0.073(4) 0.019(3) -0.002(3) -0.004(2) C23 0.030(3) 0.060(4) 0.054(4) 0.035(3) 0.010(3) 0.006(3) C24 0.032(3) 0.048(4) 0.070(4) 0.036(3) 0.013(3) 0.004(3) C25 0.033(3) 0.040(3) 0.063(4) 0.011(3) 0.006(3) -0.001(3) C26 0.034(3) 0.060(4) 0.041(3) 0.015(3) 0.001(3) 0.007(3) C27 0.044(4) 0.057(4) 0.077(5) 0.014(4) 0.016(3) 0.016(3) C28 0.058(7) 0.080(9) 0.121(11) 0.044(8) 0.028(7) 0.032(7) C28' 0.11(2) 0.12(2) 0.16(3) 0.08(2) 0.07(2) 0.07(2) C29 0.125(14) 0.065(9) 0.133(14) -0.040(9) 0.001(11) 0.018(9) C29' 0.096(12) 0.098(12) 0.102(12) 0.021(9) 0.015(9) 0.006(9) C30 0.154(17) 0.106(13) 0.146(16) 0.007(12) 0.071(13) 0.001(12) C30' 0.147(15) 0.110(14) 0.113(14) 0.054(10) 0.014(9) -0.003(9) Cu1 0.0282(5) 0.0384(6) 0.0413(6) 0.0162(4) 0.0045(4) -0.0001(4) Fe1 0.0246(4) 0.0465(5) 0.0402(5) 0.0234(4) -0.0002(3) 0.0013(3) N1 0.028(2) 0.045(3) 0.041(3) 0.014(2) 0.002(2) 0.005(2) N2 0.034(3) 0.051(3) 0.079(4) 0.029(3) -0.001(3) 0.001(2) N3 0.028(2) 0.051(3) 0.034(3) 0.014(2) 0.005(2) 0.006(2) N4 0.033(3) 0.072(4) 0.037(3) 0.027(3) -0.005(2) -0.011(2) N5 0.031(3) 0.045(3) 0.063(3) 0.034(3) -0.009(2) -0.004(2) N6 0.020(2) 0.035(3) 0.048(3) 0.015(2) -0.001(2) -0.0016(18) N7 0.022(2) 0.048(3) 0.042(3) 0.017(2) 0.001(2) 0.005(2) N8 0.019(2) 0.043(3) 0.053(3) 0.021(2) 0.005(2) 0.0020(19) N9 0.028(3) 0.046(3) 0.055(3) 0.007(2) 0.005(2) 0.006(2) O1 0.107(4) 0.075(4) 0.094(4) 0.063(3) -0.040(3) -0.025(3) O1W 0.046(11) 0.103(17) 0.16(2) 0.077(15) -0.011(11) -0.015(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.151(5) . ? C1 Fe1 1.959(5) . ? C2 N2 1.152(6) . ? C2 Fe1 1.959(6) . ? C3 N3 1.156(6) . ? C3 Fe1 1.952(6) . ? C4 N4 1.378(8) . ? C4 C5 1.395(10) . ? C4 C9 1.415(9) . ? C5 C6 1.371(9) . ? C5 H5 0.9500 . ? C6 C7 1.434(11) . ? C6 H6 0.9500 . ? C7 C8 1.338(14) . ? C7 H7 0.9500 . ? C8 C9 1.386(13) . ? C8 H8 0.9500 . ? C9 C10 1.388(13) . ? C10 C11 1.347(13) . ? C10 H10 0.9500 . ? C11 C12 1.419(10) . ? C11 H11 0.9500 . ? C12 N4 1.336(7) . ? C12 C13 1.493(11) . ? C13 O1 1.231(8) . ? C13 N5 1.351(7) . ? C14 C15 1.387(8) . ? C14 N5 1.396(7) . ? C14 C22 1.405(9) . ? C15 C16 1.390(11) . ? C15 H15 0.9500 . ? C16 C17 1.357(11) . ? C16 H16 0.9500 . ? C17 C18 1.433(9) . ? C17 H17 0.9500 . ? C18 C19 1.383(10) . ? C18 C22 1.401(9) . ? C19 C20 1.366(9) . ? C19 H19 0.9500 . ? C20 C21 1.406(8) . ? C20 H20 0.9500 . ? C21 N6 1.309(6) . ? C21 H21 0.9500 . ? C22 N6 1.382(6) . ? C23 N7 1.476(6) . ? C23 C24 1.502(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N8 1.486(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N9 1.438(7) . ? C25 N8 1.496(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 N9 1.428(7) . ? C26 N7 1.487(6) 2_676 ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.449(13) . ? C27 N9 1.482(7) . ? C27 C28' 1.511(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C27 H27C 0.7329 . ? C27 H27D 1.0086 . ? C28 C29 1.510(18) . ? C28 H27C 1.0660 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28' C29' 1.499(5) . ? C28' H28C 0.9900 . ? C28' H28D 0.9900 . ? C29 C30 1.591(15) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29' C30' 1.497(5) . ? C29' H29C 0.9900 . ? C29' H29D 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C30' H30G 0.9288 . ? C30' H30D 1.0230 . ? C30' H30F 0.9944 . ? Cu1 N8 2.001(4) 2_676 ? Cu1 N8 2.001(4) . ? Cu1 N7 2.0056 . ? Cu1 N7 2.006(4) 2_676 ? Fe1 N5 1.8883 . ? Fe1 N6 1.9770 . ? Fe1 N4 2.0096 . ? N7 C26 1.487(6) 2_676 ? N7 H7A 0.9294 . ? N8 H8A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 Fe1 173.6(4) . . ? N2 C2 Fe1 177.9(4) . . ? N3 C3 Fe1 178.1(4) . . ? N4 C4 C5 121.2(5) . . ? N4 C4 C9 120.0(7) . . ? C5 C4 C9 118.8(7) . . ? C6 C5 C4 121.2(7) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 118.4(9) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 121.0(9) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.9(9) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 120.7(8) . . ? C8 C9 C4 119.8(9) . . ? C10 C9 C4 119.5(8) . . ? C11 C10 C9 119.6(8) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 119.8(9) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? N4 C12 C11 121.6(8) . . ? N4 C12 C13 116.4(5) . . ? C11 C12 C13 122.0(7) . . ? O1 C13 N5 127.2(8) . . ? O1 C13 C12 122.4(7) . . ? N5 C13 C12 110.4(5) . . ? C15 C14 N5 127.6(6) . . ? C15 C14 C22 119.7(7) . . ? N5 C14 C22 112.7(5) . . ? C14 C15 C16 119.1(8) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 122.0(7) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 120.8(8) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C22 117.7(6) . . ? C19 C18 C17 125.6(7) . . ? C22 C18 C17 116.6(7) . . ? C20 C19 C18 120.1(6) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.3(6) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? N6 C21 C20 122.3(5) . . ? N6 C21 H21 118.9 . . ? C20 C21 H21 118.9 . . ? N6 C22 C18 121.9(6) . . ? N6 C22 C14 116.4(5) . . ? C18 C22 C14 121.7(6) . . ? N7 C23 C24 107.6(4) . . ? N7 C23 H23A 110.2 . . ? C24 C23 H23A 110.2 . . ? N7 C23 H23B 110.2 . . ? C24 C23 H23B 110.2 . . ? H23A C23 H23B 108.5 . . ? N8 C24 C23 107.1(4) . . ? N8 C24 H24A 110.3 . . ? C23 C24 H24A 110.3 . . ? N8 C24 H24B 110.3 . . ? C23 C24 H24B 110.3 . . ? H24A C24 H24B 108.5 . . ? N9 C25 N8 113.8(4) . . ? N9 C25 H25A 108.8 . . ? N8 C25 H25A 108.8 . . ? N9 C25 H25B 108.8 . . ? N8 C25 H25B 108.8 . . ? H25A C25 H25B 107.7 . . ? N9 C26 N7 114.5(4) . 2_676 ? N9 C26 H26A 108.6 . . ? N7 C26 H26A 108.6 2_676 . ? N9 C26 H26B 108.6 . . ? N7 C26 H26B 108.6 2_676 . ? H26A C26 H26B 107.6 . . ? C28 C27 N9 113.4(7) . . ? C28 C27 C28' 76.9(12) . . ? N9 C27 C28' 114.4(6) . . ? C28 C27 H27A 108.9 . . ? N9 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? N9 C27 H27B 108.9 . . ? C28' C27 H27B 129.3 . . ? H27A C27 H27B 107.7 . . ? C28 C27 H27C 45.1 . . ? N9 C27 H27C 92.6 . . ? C28' C27 H27C 122.0 . . ? H27A C27 H27C 152.6 . . ? H27B C27 H27C 79.7 . . ? C28 C27 H27D 153.2 . . ? N9 C27 H27D 91.3 . . ? C28' C27 H27D 103.1 . . ? H27A C27 H27D 70.0 . . ? H27B C27 H27D 50.1 . . ? H27C C27 H27D 127.8 . . ? C27 C28 C29 113.9(11) . . ? C29 C28 H27C 127.9 . . ? C27 C28 H28A 108.8 . . ? C29 C28 H28A 108.8 . . ? H27C C28 H28A 79.7 . . ? C27 C28 H28B 108.8 . . ? C29 C28 H28B 108.8 . . ? H27C C28 H28B 117.3 . . ? H28A C28 H28B 107.7 . . ? C29' C28' C27 118.5(10) . . ? C29' C28' H28C 107.7 . . ? C27 C28' H28C 107.7 . . ? C29' C28' H28D 107.7 . . ? C27 C28' H28D 107.7 . . ? H28C C28' H28D 107.1 . . ? C28 C29 C30 110.9(12) . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 108.0 . . ? C30' C29' C28' 113.8(5) . . ? C30' C29' H29C 108.8 . . ? C28' C29' H29C 108.8 . . ? C30' C29' H29D 108.8 . . ? C28' C29' H29D 108.8 . . ? H29C C29' H29D 107.7 . . ? C29' C30' H30G 113.0 . . ? C29' C30' H30D 108.7 . . ? H30G C30' H30D 110.0 . . ? C29' C30' H30F 107.2 . . ? H30G C30' H30F 112.6 . . ? H30D C30' H30F 105.0 . . ? N8 Cu1 N8 180.0 2_676 . ? N8 Cu1 N7 94.12(15) 2_676 . ? N8 Cu1 N7 85.88(15) . . ? N8 Cu1 N7 85.88(15) 2_676 2_676 ? N8 Cu1 N7 94.12(16) . 2_676 ? N7 Cu1 N7 180.0 . 2_676 ? N5 Fe1 C3 96.66(15) . . ? N5 Fe1 C1 171.78(15) . . ? C3 Fe1 C1 90.5(2) . . ? N5 Fe1 C2 91.60(16) . . ? C3 Fe1 C2 171.7(2) . . ? C1 Fe1 C2 81.2(2) . . ? N5 Fe1 N6 82.9 . . ? C3 Fe1 N6 90.22(15) . . ? C1 Fe1 N6 93.18(15) . . ? C2 Fe1 N6 91.19(17) . . ? N5 Fe1 N4 82.0 . . ? C3 Fe1 N4 91.22(15) . . ? C1 Fe1 N4 101.87(15) . . ? C2 Fe1 N4 89.55(17) . . ? N6 Fe1 N4 164.9 . . ? C12 N4 C4 119.0(4) . . ? C12 N4 Fe1 110.2(3) . . ? C4 N4 Fe1 130.6(3) . . ? C13 N5 C14 125.3(4) . . ? C13 N5 Fe1 116.7(4) . . ? C14 N5 Fe1 116.2(3) . . ? C21 N6 C22 118.5(4) . . ? C21 N6 Fe1 129.7(3) . . ? C22 N6 Fe1 111.7(3) . . ? C23 N7 C26 112.7(4) . 2_676 ? C23 N7 Cu1 106.9(3) . . ? C26 N7 Cu1 115.6(2) 2_676 . ? C23 N7 H7A 107.0 . . ? C26 N7 H7A 107.1 2_676 . ? Cu1 N7 H7A 107.1 . . ? C24 N8 C25 112.3(4) . . ? C24 N8 Cu1 106.9(3) . . ? C25 N8 Cu1 114.1(4) . . ? C24 N8 H8A 107.9 . . ? C25 N8 H8A 107.6 . . ? Cu1 N8 H8A 107.7 . . ? C26 N9 C25 115.8(5) . . ? C26 N9 C27 114.9(5) . . ? C25 N9 C27 116.7(5) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.072 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 948660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H67.5 Cu Fe2 N18 O6.75' _chemical_formula_weight 1300.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.350(2) _cell_length_b 12.023(3) _cell_length_c 12.921(3) _cell_angle_alpha 101.583(3) _cell_angle_beta 94.969(3) _cell_angle_gamma 94.440(3) _cell_volume 1561.8(6) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4085 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 667 _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8196 _exptl_absorpt_correction_T_max 0.8463 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11219 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5437 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.The restraints that were used for the refinement of the disorder of the unique n-propyl group (C28,C29) are: isor 0.01 C28 C28' C29 C29' dfix 1.5 0.005 C27 C28 C28 C29 C27 C28' C28' C29' dfix 2.5 0.005 C27 C29 The water oxygen atoms seem to be partially presented in the crystal lattice, so individual free-variables ( with partial occupancy) are allowed to refine for each of these water oxygen atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.0494P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5437 _refine_ls_number_parameters 418 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1880(3) 0.0528(3) 0.3945(3) 0.0308(8) Uani 1 1 d . . . C2 C -0.0713(3) 0.0407(3) 0.3089(3) 0.0312(8) Uani 1 1 d . . . C3 C 0.2457(3) 0.2504(3) 0.3597(3) 0.0328(8) Uani 1 1 d . . . C4 C 0.1539(3) 0.0150(3) 0.1202(3) 0.0369(9) Uani 1 1 d . . . C5 C 0.1614(3) -0.0837(3) 0.1614(3) 0.0389(9) Uani 1 1 d . . . H5 H 0.1384 -0.0833 0.2310 0.047 Uiso 1 1 calc R . . C6 C 0.2014(4) -0.1810(4) 0.1034(3) 0.0506(11) Uani 1 1 d . . . H6 H 0.2041 -0.2477 0.1320 0.061 Uiso 1 1 calc R . . C7 C 0.2385(4) -0.1811(5) 0.0005(3) 0.0623(14) Uani 1 1 d . . . H7 H 0.2694 -0.2475 -0.0389 0.075 Uiso 1 1 calc R . . C8 C 0.2306(4) -0.0882(5) -0.0425(3) 0.0600(13) Uani 1 1 d . . . H8 H 0.2553 -0.0904 -0.1119 0.072 Uiso 1 1 calc R . . C9 C 0.1860(4) 0.0132(4) 0.0145(3) 0.0466(10) Uani 1 1 d . . . C10 C 0.1690(4) 0.1084(4) -0.0300(3) 0.0554(12) Uani 1 1 d . . . H10 H 0.1938 0.1096 -0.0989 0.067 Uiso 1 1 calc R . . C11 C 0.1173(4) 0.1987(4) 0.0254(3) 0.0533(12) Uani 1 1 d . . . H11 H 0.1019 0.2624 -0.0055 0.064 Uiso 1 1 calc R . . C12 C 0.0863(4) 0.1980(3) 0.1288(3) 0.0429(10) Uani 1 1 d . . . C13 C 0.0189(4) 0.2913(3) 0.1892(3) 0.0446(10) Uani 1 1 d . . . C14 C -0.0729(3) 0.3382(3) 0.3585(3) 0.0396(9) Uani 1 1 d . . . C15 C -0.1511(4) 0.4229(3) 0.3443(4) 0.0506(11) Uani 1 1 d . . . H15 H -0.1672 0.4409 0.2763 0.061 Uiso 1 1 calc R . . C16 C -0.2067(4) 0.4826(3) 0.4329(4) 0.0582(13) Uani 1 1 d . . . H16 H -0.2624 0.5395 0.4226 0.070 Uiso 1 1 calc R . . C17 C -0.1840(4) 0.4618(3) 0.5315(4) 0.0524(11) Uani 1 1 d . . . H17 H -0.2215 0.5053 0.5891 0.063 Uiso 1 1 calc R . . C18 C -0.1047(4) 0.3759(3) 0.5491(3) 0.0431(10) Uani 1 1 d . . . C19 C -0.0742(4) 0.3475(3) 0.6483(3) 0.0451(10) Uani 1 1 d . . . H19 H -0.1059 0.3887 0.7101 0.054 Uiso 1 1 calc R . . C20 C 0.0008(4) 0.2611(3) 0.6552(3) 0.0443(10) Uani 1 1 d . . . H20 H 0.0212 0.2413 0.7219 0.053 Uiso 1 1 calc R . . C21 C 0.0482(3) 0.2010(3) 0.5639(3) 0.0379(9) Uani 1 1 d . . . H21 H 0.0992 0.1398 0.5702 0.046 Uiso 1 1 calc R . . C22 C -0.0509(3) 0.3129(3) 0.4610(3) 0.0357(8) Uani 1 1 d . . . C23 C 0.4106(4) -0.2343(3) 0.3841(3) 0.0439(10) Uani 1 1 d . . . H23A H 0.4002 -0.3164 0.3860 0.053 Uiso 1 1 calc R . . H23B H 0.3226 -0.2103 0.3698 0.053 Uiso 1 1 calc R . . C24 C 0.3891(4) -0.1854(3) 0.5764(3) 0.0416(9) Uani 1 1 d . . . H24A H 0.3954 -0.2626 0.5912 0.050 Uiso 1 1 calc R . . H24B H 0.2966 -0.1775 0.5553 0.050 Uiso 1 1 calc R . . C25 C 0.4394(4) -0.0961(3) 0.6738(3) 0.0422(9) Uani 1 1 d . . . H25A H 0.3830 -0.1002 0.7314 0.051 Uiso 1 1 calc R . . H25B H 0.5290 -0.1087 0.6992 0.051 Uiso 1 1 calc R . . C26 C 0.5099(4) 0.1100(3) 0.7275(3) 0.0431(10) Uani 1 1 d . . . H26A H 0.4685 0.1134 0.7942 0.052 Uiso 1 1 calc R . . H26B H 0.6003 0.0909 0.7411 0.052 Uiso 1 1 calc R . . C27 C 0.3970(4) 0.2782(4) 0.7107(4) 0.0652(13) Uani 1 1 d D . . H27A H 0.3353 0.2369 0.7470 0.078 Uiso 0.202(9) 1 d PR B 1 H27B H 0.3554 0.2763 0.6380 0.078 Uiso 0.202(9) 1 d PR B 1 H27C H 0.3210 0.2258 0.6773 0.078 Uiso 0.798(9) 1 d PR B 2 H27D H 0.4034 0.3437 0.6753 0.078 Uiso 0.798(9) 1 d PR B 2 C28 C 0.418(3) 0.4016(8) 0.7715(15) 0.128(3) Uani 0.202(9) 1 d PDU B 1 H28A H 0.4732 0.4432 0.7303 0.153 Uiso 0.202(9) 1 calc PR B 1 H28B H 0.3315 0.4319 0.7673 0.153 Uiso 0.202(9) 1 calc PR B 1 C29 C 0.475(3) 0.439(2) 0.8869(15) 0.157(11) Uani 0.30 1 d PDU B 1 H29A H 0.4806 0.5221 0.9061 0.235 Uiso 0.202(9) 1 d PR B 1 H29B H 0.5626 0.4135 0.8943 0.235 Uiso 0.202(9) 1 d PR B 1 H29C H 0.4206 0.4063 0.9341 0.235 Uiso 0.202(9) 1 d PR B 1 C28' C 0.3781(10) 0.3202(8) 0.8288(5) 0.128(3) Uani 0.798(9) 1 d PDU B 2 H28C H 0.3536 0.2507 0.8555 0.153 Uiso 0.798(9) 1 calc PR B 2 H28D H 0.4659 0.3504 0.8646 0.153 Uiso 0.798(9) 1 calc PR B 2 C29' C 0.2877(12) 0.4060(10) 0.8731(10) 0.169(5) Uani 0.70 1 d PDU B 2 H29D H 0.3145 0.4803 0.8573 0.254 Uiso 0.798(9) 1 d PR B 2 H29E H 0.2923 0.4128 0.9502 0.254 Uiso 0.798(9) 1 d PR B 2 H29F H 0.1981 0.3807 0.8414 0.254 Uiso 0.798(9) 1 d PR B 2 Cu1 Cu 0.5000 0.0000 0.5000 0.03105(18) Uani 1 2 d S . . Fe1 Fe 0.08024(4) 0.15379(4) 0.33130(4) 0.02996(17) Uani 1 1 d . . . N1 N 0.2597(3) 0.0021(2) 0.4351(2) 0.0347(7) Uani 1 1 d . . . N2 N -0.1628(3) -0.0236(3) 0.2958(2) 0.0367(7) Uani 1 1 d . . . N3 N 0.3440(3) 0.3064(3) 0.3808(3) 0.0453(8) Uani 1 1 d . . . N4 N 0.1096(3) 0.1116(3) 0.1778(2) 0.0353(7) Uani 1 1 d . . . N5 N -0.0081(3) 0.2689(3) 0.2836(2) 0.0360(7) Uani 1 1 d . . . N6 N 0.0247(3) 0.2262(2) 0.4690(2) 0.0326(7) Uani 1 1 d . . . N7 N 0.4690(3) -0.1694(2) 0.4900(2) 0.0347(7) Uani 1 1 d . . . H7A H 0.5493 -0.1961 0.5041 0.042 Uiso 1 1 calc R . . N8 N 0.4386(3) 0.0169(2) 0.6449(2) 0.0346(7) Uani 1 1 d . . . H8A H 0.3521 0.0329 0.6384 0.042 Uiso 1 1 calc R . . N9 N 0.5147(3) 0.2198(3) 0.7023(3) 0.0446(8) Uani 1 1 d . . . O1 O -0.0081(3) 0.3746(3) 0.1521(2) 0.0633(9) Uani 1 1 d . . . O2 O 0.5498(16) 0.5551(13) 0.7579(13) 0.326(10) Uani 0.745(18) 1 d P C 1 O3 O 0.749(2) 0.4729(13) 0.8604(12) 0.216(8) Uani 0.390(11) 1 d P D 1 O4 O 0.5041(14) 0.4679(13) 0.5638(13) 0.073(7) Uani 0.219(10) 1 d P A 2 O5 O 0.9708(19) 0.4338(10) 0.9346(9) 0.216(8) Uani 0.524(13) 1 d P E 2 O6 O 0.509(2) 0.679(2) 0.848(2) 0.326(10) Uani 0.495(16) 1 d P F 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0225(18) 0.0354(19) 0.0333(19) 0.0036(15) 0.0056(15) 0.0011(16) C2 0.0251(19) 0.042(2) 0.0310(18) 0.0109(15) 0.0072(15) 0.0156(17) C3 0.029(2) 0.0330(19) 0.040(2) 0.0115(16) 0.0045(16) 0.0136(17) C4 0.0184(18) 0.056(2) 0.0335(19) 0.0056(17) -0.0006(15) -0.0008(17) C5 0.0251(19) 0.053(2) 0.035(2) 0.0032(18) 0.0001(15) 0.0075(17) C6 0.035(2) 0.066(3) 0.044(2) -0.005(2) -0.0029(18) 0.013(2) C7 0.037(3) 0.084(4) 0.051(3) -0.021(3) -0.003(2) 0.016(2) C8 0.036(2) 0.093(4) 0.044(2) 0.000(3) 0.0068(19) 0.006(2) C9 0.028(2) 0.072(3) 0.035(2) 0.005(2) 0.0029(16) -0.004(2) C10 0.043(3) 0.087(4) 0.036(2) 0.018(2) 0.0056(19) -0.012(2) C11 0.048(3) 0.072(3) 0.043(2) 0.028(2) -0.003(2) -0.012(2) C12 0.032(2) 0.054(2) 0.044(2) 0.0202(19) -0.0052(17) -0.0060(19) C13 0.033(2) 0.041(2) 0.059(3) 0.019(2) -0.0110(19) -0.0020(18) C14 0.0211(18) 0.0295(19) 0.068(3) 0.0123(18) -0.0001(17) 0.0020(15) C15 0.037(2) 0.034(2) 0.081(3) 0.017(2) -0.005(2) -0.0014(18) C16 0.032(2) 0.031(2) 0.110(4) 0.008(2) 0.006(2) 0.0083(18) C17 0.037(2) 0.029(2) 0.090(4) 0.005(2) 0.017(2) 0.0050(18) C18 0.0243(19) 0.029(2) 0.072(3) -0.0015(19) 0.0121(19) -0.0029(16) C19 0.035(2) 0.039(2) 0.057(3) -0.0041(19) 0.0172(19) -0.0045(18) C20 0.039(2) 0.046(2) 0.045(2) 0.0022(18) 0.0093(18) -0.0015(19) C21 0.031(2) 0.043(2) 0.040(2) 0.0064(17) 0.0069(16) 0.0066(17) C22 0.0187(17) 0.0293(19) 0.058(2) 0.0072(17) 0.0037(16) 0.0023(15) C23 0.028(2) 0.036(2) 0.063(3) 0.0036(19) 0.0021(18) -0.0013(17) C24 0.029(2) 0.038(2) 0.062(3) 0.0195(19) 0.0095(18) 0.0035(17) C25 0.031(2) 0.051(2) 0.052(2) 0.0230(19) 0.0127(18) 0.0153(18) C26 0.030(2) 0.058(3) 0.037(2) -0.0001(18) 0.0010(16) 0.0059(19) C27 0.044(3) 0.047(3) 0.106(4) 0.007(3) 0.028(3) 0.013(2) C28 0.127(6) 0.117(6) 0.160(6) 0.030(4) 0.093(5) 0.050(5) C29 0.147(13) 0.159(14) 0.153(13) 0.001(9) 0.012(9) 0.037(10) C28' 0.127(6) 0.117(6) 0.160(6) 0.030(4) 0.093(5) 0.050(5) C29' 0.169(9) 0.158(8) 0.182(9) 0.035(7) 0.022(7) 0.022(7) Cu1 0.0258(3) 0.0316(3) 0.0355(3) 0.0067(3) 0.0040(3) 0.0009(3) Fe1 0.0204(3) 0.0344(3) 0.0365(3) 0.0104(2) 0.0012(2) 0.0064(2) N1 0.0280(16) 0.0382(17) 0.0392(17) 0.0084(14) 0.0028(13) 0.0108(14) N2 0.0268(17) 0.0475(19) 0.0374(17) 0.0106(14) 0.0071(13) 0.0051(16) N3 0.0283(18) 0.0351(17) 0.073(2) 0.0114(16) 0.0023(16) 0.0070(15) N4 0.0228(15) 0.0469(19) 0.0355(16) 0.0092(14) -0.0019(13) 0.0024(14) N5 0.0249(16) 0.0407(18) 0.0439(18) 0.0155(14) -0.0031(13) 0.0030(13) N6 0.0221(15) 0.0308(16) 0.0447(18) 0.0069(13) 0.0031(13) 0.0052(13) N7 0.0206(15) 0.0359(16) 0.0486(18) 0.0092(14) 0.0051(13) 0.0058(13) N8 0.0218(15) 0.0420(18) 0.0418(17) 0.0102(14) 0.0044(13) 0.0095(13) N9 0.0321(18) 0.0420(19) 0.056(2) -0.0024(16) 0.0127(15) 0.0047(15) O1 0.070(2) 0.0550(19) 0.072(2) 0.0358(16) -0.0045(16) 0.0034(16) O2 0.364(19) 0.254(14) 0.40(2) 0.096(13) 0.210(15) 0.002(13) O3 0.40(2) 0.119(7) 0.135(9) 0.053(6) 0.000(9) -0.005(9) O4 0.042(9) 0.077(12) 0.101(13) 0.020(9) 0.008(8) 0.009(8) O5 0.40(2) 0.119(7) 0.135(9) 0.053(6) 0.000(9) -0.005(9) O6 0.364(19) 0.254(14) 0.40(2) 0.096(13) 0.210(15) 0.002(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.153(4) . ? C1 Fe1 1.958(4) . ? C2 N2 1.153(4) . ? C2 Fe1 1.955(4) . ? C3 N3 1.155(4) . ? C3 Fe1 1.957(4) . ? C4 N4 1.382(5) . ? C4 C5 1.399(5) . ? C4 C9 1.430(5) . ? C5 C6 1.370(5) . ? C5 H5 0.9500 . ? C6 C7 1.416(6) . ? C6 H6 0.9500 . ? C7 C8 1.348(7) . ? C7 H7 0.9500 . ? C8 C9 1.424(6) . ? C8 H8 0.9500 . ? C9 C10 1.396(6) . ? C10 C11 1.350(6) . ? C10 H10 0.9500 . ? C11 C12 1.403(5) . ? C11 H11 0.9500 . ? C12 N4 1.347(5) . ? C12 C13 1.489(6) . ? C13 O1 1.234(4) . ? C13 N5 1.348(5) . ? C14 C15 1.380(5) . ? C14 N5 1.398(5) . ? C14 C22 1.420(5) . ? C15 C16 1.417(6) . ? C15 H15 0.9500 . ? C16 C17 1.351(6) . ? C16 H16 0.9500 . ? C17 C18 1.410(6) . ? C17 H17 0.9500 . ? C18 C19 1.407(6) . ? C18 C22 1.416(5) . ? C19 C20 1.356(5) . ? C19 H19 0.9500 . ? C20 C21 1.403(5) . ? C20 H20 0.9500 . ? C21 N6 1.328(4) . ? C21 H21 0.9500 . ? C22 N6 1.366(4) . ? C23 N9 1.444(5) 2_656 ? C23 N7 1.483(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N7 1.479(4) . ? C24 C25 1.505(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N8 1.480(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 N9 1.420(5) . ? C26 N8 1.481(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 N9 1.454(5) . ? C27 C28 1.523(5) . ? C27 C28' 1.543(5) . ? C27 H27A 0.9843 . ? C27 H27B 0.9937 . ? C27 H27C 0.9783 . ? C27 H27D 0.9880 . ? C28 C29 1.521(5) . ? C28 H27D 1.2870 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C28' H28C 0.9900 . ? C28' H28D 0.9900 . ? C29' H29D 0.9800 . ? C29' H29E 0.9800 . ? C29' H29F 0.9800 . ? Cu1 N8 2.006(3) . ? Cu1 N8 2.006(3) 2_656 ? Cu1 N7 2.014(3) . ? Cu1 N7 2.014(3) 2_656 ? Fe1 N5 1.890(3) . ? Fe1 N6 1.971(3) . ? Fe1 N4 2.001(3) . ? N7 H7A 0.9300 . ? N8 H8A 0.9300 . ? N9 C23 1.444(5) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 Fe1 173.7(3) . . ? N2 C2 Fe1 178.1(3) . . ? N3 C3 Fe1 177.0(3) . . ? N4 C4 C5 121.1(3) . . ? N4 C4 C9 119.7(4) . . ? C5 C4 C9 119.1(4) . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.1(4) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 122.6(4) . . ? C10 C9 C4 119.4(4) . . ? C8 C9 C4 118.0(4) . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 119.7(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N4 C12 C11 122.7(4) . . ? N4 C12 C13 115.8(3) . . ? C11 C12 C13 121.4(4) . . ? O1 C13 N5 127.5(4) . . ? O1 C13 C12 121.6(4) . . ? N5 C13 C12 110.9(3) . . ? C15 C14 N5 128.7(4) . . ? C15 C14 C22 119.3(4) . . ? N5 C14 C22 111.9(3) . . ? C14 C15 C16 118.7(4) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 122.7(4) . . ? C17 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 124.9(4) . . ? C19 C18 C22 117.0(3) . . ? C17 C18 C22 118.1(4) . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.0(4) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? N6 C21 C20 122.6(4) . . ? N6 C21 H21 118.7 . . ? C20 C21 H21 118.7 . . ? N6 C22 C18 122.8(4) . . ? N6 C22 C14 116.3(3) . . ? C18 C22 C14 120.9(3) . . ? N9 C23 N7 114.4(3) 2_656 . ? N9 C23 H23A 108.7 2_656 . ? N7 C23 H23A 108.7 . . ? N9 C23 H23B 108.7 2_656 . ? N7 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? N7 C24 C25 108.2(3) . . ? N7 C24 H24A 110.1 . . ? C25 C24 H24A 110.1 . . ? N7 C24 H24B 110.1 . . ? C25 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? N8 C25 C24 107.9(3) . . ? N8 C25 H25A 110.1 . . ? C24 C25 H25A 110.1 . . ? N8 C25 H25B 110.1 . . ? C24 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? N9 C26 N8 115.1(3) . . ? N9 C26 H26A 108.5 . . ? N8 C26 H26A 108.5 . . ? N9 C26 H26B 108.5 . . ? N8 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? N9 C27 C28 114.9(12) . . ? N9 C27 C28' 109.6(5) . . ? C28 C27 C28' 54.3(10) . . ? N9 C27 H27A 109.0 . . ? C28 C27 H27A 107.5 . . ? C28' C27 H27A 58.1 . . ? N9 C27 H27B 108.8 . . ? C28 C27 H27B 108.7 . . ? C28' C27 H27B 141.6 . . ? H27A C27 H27B 107.7 . . ? N9 C27 H27C 110.1 . . ? C28 C27 H27C 135.0 . . ? C28' C27 H27C 108.1 . . ? H27A C27 H27C 53.3 . . ? H27B C27 H27C 56.6 . . ? N9 C27 H27D 110.1 . . ? C28 C27 H27D 57.0 . . ? C28' C27 H27D 109.8 . . ? H27A C27 H27D 140.8 . . ? H27B C27 H27D 56.3 . . ? H27C C27 H27D 109.2 . . ? C29 C28 C27 124.2(7) . . ? C29 C28 H27D 157.7 . . ? C29 C28 H28A 106.3 . . ? C27 C28 H28A 106.3 . . ? H27D C28 H28A 73.0 . . ? C29 C28 H28B 106.3 . . ? C27 C28 H28B 106.3 . . ? H27D C28 H28B 95.0 . . ? H28A C28 H28B 106.4 . . ? C28 C29 H29A 108.0 . . ? C28 C29 H29B 109.1 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 111.3 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C29' C28' C27 126.6(8) . . ? C29' C28' H27A 119.8 . . ? C29' C28' H29C 60.0 . . ? C27 C28' H29C 148.2 . . ? H27A C28' H29C 172.0 . . ? C29' C28' H28C 105.7 . . ? C27 C28' H28C 105.7 . . ? H27A C28' H28C 71.4 . . ? H29C C28' H28C 100.8 . . ? C29' C28' H28D 105.7 . . ? C27 C28' H28D 105.7 . . ? H27A C28' H28D 133.6 . . ? H29C C28' H28D 49.1 . . ? H28C C28' H28D 106.1 . . ? C28' C29' H29C 61.1 . . ? C28' C29' H29D 109.7 . . ? H29C C29' H29D 90.3 . . ? C28' C29' H29E 108.7 . . ? H29C C29' H29E 61.8 . . ? H29D C29' H29E 109.5 . . ? C28' C29' H29F 110.0 . . ? H29C C29' H29F 160.2 . . ? H29D C29' H29F 109.5 . . ? H29E C29' H29F 109.5 . . ? N8 Cu1 N8 180.0 . 2_656 ? N8 Cu1 N7 86.19(12) . . ? N8 Cu1 N7 93.81(12) 2_656 . ? N8 Cu1 N7 93.81(12) . 2_656 ? N8 Cu1 N7 86.19(12) 2_656 2_656 ? N7 Cu1 N7 180.0 . 2_656 ? N5 Fe1 C3 91.91(13) . . ? N5 Fe1 C2 96.08(13) . . ? C3 Fe1 C2 172.01(13) . . ? N5 Fe1 C1 171.61(13) . . ? C3 Fe1 C1 80.94(14) . . ? C2 Fe1 C1 91.13(14) . . ? N5 Fe1 N6 82.57(12) . . ? C3 Fe1 N6 91.63(13) . . ? C2 Fe1 N6 89.82(13) . . ? C1 Fe1 N6 93.20(13) . . ? N5 Fe1 N4 82.08(13) . . ? C3 Fe1 N4 89.60(13) . . ? C2 Fe1 N4 91.08(13) . . ? C1 Fe1 N4 102.12(13) . . ? N6 Fe1 N4 164.63(12) . . ? C12 N4 C4 118.5(3) . . ? C12 N4 Fe1 110.6(3) . . ? C4 N4 Fe1 130.9(2) . . ? C13 N5 C14 125.4(3) . . ? C13 N5 Fe1 116.8(3) . . ? C14 N5 Fe1 116.4(2) . . ? C21 N6 C22 117.9(3) . . ? C21 N6 Fe1 129.5(2) . . ? C22 N6 Fe1 112.6(2) . . ? C24 N7 C23 112.9(3) . . ? C24 N7 Cu1 106.6(2) . . ? C23 N7 Cu1 114.1(2) . . ? C24 N7 H7A 107.7 . . ? C23 N7 H7A 107.7 . . ? Cu1 N7 H7A 107.7 . . ? C26 N8 C25 113.0(3) . . ? C26 N8 Cu1 115.4(2) . . ? C25 N8 Cu1 107.0(2) . . ? C26 N8 H8A 107.0 . . ? C25 N8 H8A 107.0 . . ? Cu1 N8 H8A 107.0 . . ? C26 N9 C23 115.6(3) . 2_656 ? C26 N9 C27 117.0(3) . . ? C23 N9 C27 116.5(3) 2_656 . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.533 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 948661'